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ISSN 0265-4245 5608256303 January 2005
Graphical abstracts ofnew developments
www.rsc.org/mos
METHODS INORGANIC SYNTHESIS
CONTENTS
Editorial . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2
Angewandte Chemie, International Edition . . . . . . . . . . . . . . . . . 3Chemical Communications . . . . . . . . . . . . . . . . . . . . . . . . 4European Journal of Organic Chemistry . . . . . . . . . . . . . . . . . . 8Helvetica Chimica Acta . . . . . . . . . . . . . . . . . . . . . . . . . . 8Journal of Organic Chemistry . . . . . . . . . . . . . . . . . . . . . . . 8Journal of the American Chemical Society . . . . . . . . . . . . . . . . 10New Journal of Chemistry . . . . . . . . . . . . . . . . . . . . . . . 15Organic & Biomolecular Chemistry . . . . . . . . . . . . . . . . . . . . 15Organic Letters . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23Synthetic Communications . . . . . . . . . . . . . . . . . . . . . . . 27Tetrahedron . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33Tetrahedron Letters . . . . . . . . . . . . . . . . . . . . . . . . . . 35
Books, Reviews and Conference Proceedings . . . . . . . . . . . . . . . 40
Author Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41Reagent Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43Reaction Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . 45Reactant Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46Product Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47
Journal Selection . . . . . . . . . . . . . . . . . . . . . . . . . . . 49Abbreviations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 50
Royal Society of Chemistry 2005
Editorial
2 METHODS IN ORGANIC SYNTHESIS January 2005
Editorial
Structure-searchable access to Methods in Organic Synthesis
Welcome to your new look Methods in Organic Synthesis. The design and layout of the print version have been modernised, following positive feedback about the design of the sister title Catalysts & Catalysed Reactions. I hope that you find the new design easier to browse in print.
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Dr Graham McCann CSci CChem MRSC Managing Editor, Methods in Organic Synthesis www.rsc.org/mos mos@rsc.org
Angewandte Chemie, International Edition
Angewandte Chemie, International Edition
56082 A practical and mild method for the highly selective conversion of terminal alkenes into aldehydesthrough epoxidationisomerization with ruthenium(IV)catalystsJ. Chen, C.-M. Che*, Angew. Chem., Int. Ed., 2004, 43(37), 4950-4954
catalyst
CDCl3, 60 C, 2 h14 examples (8199%) 96%
CHO2,6-dichloropyridine N-oxide,
air
RuCl
Cl
catalyst =
56083 Enantioselective hydrogenation of -ketoesters with monodentate ligandsK. Junge, B. Hagemann, S. Enthaler, G. Oehme, M. Michalik, X. Monsees, T. Riermeier, U. Dingerdissen, M. Beller*, Angew.Chem., Int. Ed., 2004, 43(38), 5066-5069
80 C, H2 (60 bar), 16 h
>99%, 28% ee (S)38 examples (28>99%, 295% ee)
[L2RuBr2]H3C OCH3
O O
H3C OCH3
OH O
OO
P OPhL =
56084 Difluoromethyl phenyl sulfone, a difluoromethylidene equivalent: use in the synthesis of1,1-difluoro-1-alkenesG. K. S. Prakash*, J. Hu, Y. Wang, G. A. Olah, Angew. Chem., Int. Ed., 2004, 43(39), 5203-5206
The alkyl-substituted difluoromethyl sulfones can be synthesized from difluoromethyl phenyl sulfone, theappropriate alkyl iodide and potassium tert-butoxide (13 examples, 3784%)
THF, 20 C rt
87%8 examples (5588%)
tBuOKPhO SO2Ph PhO
56085 Evidence for the formation of an iodosylbenzene(salen)iron(III)-catalyzed asymmetric sulfide oxidationK. P. Bryliakov*, E. P. Talsi, Angew. Chem., Int. Ed., 2004, 43(39), 5228-5230
CH2Cl2, 0 C, 2 h
94% conversion,92% selectivity,
58% ee (S)-()-isomer3 examples (7466% conversion,
catalystPh S
PhPh S
Ph
O
6999% selectivity,2062% ee)
N N
O OFe
Cl
H H
catalyst =
PhIO
56086 Development of a ruthenium-catalyzed asymmetric epoxidation procedure with hydrogen peroxide asthe oxidantM. K. Tse, C. Dobler, S. Bhor, M. Klawonn, W. Magerlein, H. Hugl, M. Beller*, Angew. Chem., Int. Ed., 2004, 43(39), 5255-5260
tBuOH, rt, 12 h
12 examples (59100% yield, 72100% selectivity, 2884% ee)
30% aq. H2O2Ph Ph
Ocatalyst
93% yield93% selectivity
80% ee
catalyst =
NO
N N
O
Ru
NO
O
O
O
METHODS IN ORGANIC SYNTHESIS January 2005 3
Angewandte Chemie, International Edition
56087 Gold(I)-catalyzed 5-endo-dig carbocyclization of acetylenic dicarbonyl compoundsS. T. Staben, J. J. Kennedy-Smith, F. D. Toste*, Angew. Chem., Int. Ed., 2004, 43(40), 5350-5352
CH2Cl2, rt, 5 min
83%12 examples (7499%)
[Au(PPh3)]Cl, AgOTfOMe
O O
MeO
O
O
56088 Ru- and Rh-catalyzed CC bond cleavage of cyclobutanones: reconstructive and selective synthesis of2-pyranones, cyclopentenes, and cyclohexenonesT. Kondo, Y. Taguchi, Y. Kaneko, M. Niimi, T. Mitsudo*, Angew. Chem., Int. Ed., 2004, 43(40), 5369-5372
toluene, 100 C, 2 h
86%4 examples (7586%)
[RhCl(CO)2]2 or [RuCl2(CO)3]2O O
O
56089 Carboamination: additions of imine C1N bonds across alkynes catalyzed by imidozirconium complexesR. T. Ruck, R. L. Zuckermann, S. W. Krska, R. G. Bergmann*, Angew. Chem., Int. Ed., 2004, 43(40), 5372-5374
C6D6, 145 C, 3096 h80%7 examples (5885%)
NNCp2Zr N
Ph Ph
OMe
O
Ph
O
Ph
PhPh
56090 Zirconium-mediated conversion of amides to nitriles: a surprising additive effectR. T. Ruck, R. G. Bergmann*, Angew. Chem., Int. Ed., 2004, 43(40), 5375-5377
[D8]THF, 105 C, 48 h8 examples (91100%)
Cp2ZrMe2NH2
O
96%
LiClCN
56091 Electrophilic alkylations in neutral aqueous or alcoholic solutionsM. Hoffmann, N. Hampel, T. Kanzian, H. Mayr*, Angew. Chem., Int. Ed., 2004, 43(40), 5402-5405
CF3CH2OH, rt
70%19 examples (33100%)
2,6-lutidineCl
MeO MeO
OO
Chemical Communications
56092 Direct arylation of aromatic CH bonds catalyzed by Cp*Ir complexesK.-i. Fujita*, M. Nonogawa, R. Yamaguchi*, Chem. Commun., 2004, (17), 1926-1927
[5-C5Me5IrHCl]2KOtBu, 80 C, 30 h
9 examples (3272%) 70%
I
4 METHODS IN ORGANIC SYNTHESIS January 2005
Chemical Communications
56093 First catalytic asymmetric synthesis of -amino--polyfluoroalkyl ketones via proline-catalysed directasymmetric carboncarbon bond formation reaction of polyfluoroalkylated aldiminesK. Funabiki*, M. Nagamori, S. Goushi, M. Matsui, Chem. Commun., 2004, (17), 1928-1929
L-prolineacetone, rt, 7 d
19 examples (ee 20.498.0%) 98% ee, 71% yield, 99 : 1 = S : RC6H4OMe-p
O
F2HC
NH Op-MeOC6H4F
F
56094 A highly efficient gold/silver-catalyzed addition of arenes to iminesY. Luo, C.-J. Li*, Chem. Commun., 2004, (17), 1930-1931
CH2Cl2, 0 C, 12 h
9 examples (3485%) 85%
AuCl3AgOTf
OMe
MeO OMeEtO2CHC NTs
OMe
MeO OMe
CO2Et
NHTs
56095 CuI-catalyzed coupling reaction of aryl halides with terminal alkynes in the absence of palladium andphosphineD. Ma*, F. Liu, Chem. Commun., 2004, (17), 1934-1935
CuIN,N-dimethylglycineK2CO3, DMF, 100 C, 24 h
26 examples (6098%) 98%
H3-NO2C6H4I 3-NO2C6H4Ph Ph
56096 Radical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of -amino acidsemploying carbohydrate-based chiral auxiliariesS. A. Johannesen, S. Albu, R. G. Hazell, T. Skrydstrup*, Chem. Commun., 2004, (17), 1962-1963
THF, 78 C, 20 h
9 examples (5480%) 71%, >95 : 5 ds
SmI2O
Cy
N O
OO
O
OnBuO
Cy
N HO
OO
O
OnBu
56097 (Bu3Sn)2TBAF: a new combination reagent for the reduction and deuteration of aryl bromides and iodidesD. C. Harrowven*, I. L. Guy, M. I. T. Nunn, Chem. Commun., 2004, (17), 1966-1967
(Bu3Sn)2TBAFPhMe, 90 C, 1 h
13 examples (9099%) 97%
O
O
HSS
Br
O
O
HSS
56098 Palladium catalysed cross-coupling reactions of silylaminesC. J. Smith*, T. R. Early, A. B. Holmes*, R. E. Shute, Chem. Commun., 2004, (17), 1976-1977
Pd(OAc)2,P(t-Bu)2(o-biphen)Sc2Co3, scCO2,
100 C, 17 h
18 examples (2584%) 84%
CO2Me
NTMS
CO2Me
Br
MeO2C CO2Me
N
METHODS IN ORGANIC SYNTHESIS January 2005 5
Chemical Communications
56099 A highly efficient heterogeneous catalytic system for Heck reactions with a palladium colloid layerreduced in situ in the channel of mesoporous silica materialsL. Li, J.-l. Shi*, J.-n. Yan, Chem. Commun., 2004, (17), 1990-1991
NEt3, 120 C, 50 min
8 examples (conversion 37100%, yield 8599%) 100% conversion, 99% yield
Pd-SBABr COMe
PhMeOC
Ph
56100 Highly efficient and recyclable heterogeneous asymmetric transfer hydrogenation of ketones in waterP. N. Liu, J. G. Deng, Y. Q. Tu*, S. H. Wang, Chem. Commun., 2004, (18), 2070-2071
[RuCl2(p-cymene)]2silica gelBu4NBr, HCO2Na, 311 h
11 substrate examples (ee 90>99%) >99% conversion, 94% eeCl
O
Cl
OH
56101 First example of ring expansion of activated quinolines and isoquinolines: novel benzoazepinesJ. S. Yadav*, B. V. Subba Reddy, M. K. Gupta, A. Prabhakar, B. Jagadeesh, Chem. Commun., 2004, (18), 2124-2125
1,2-dichloroethane,reflux, 0.5 h
11 examples (8098%) 98%
Cu(OTf)2N O
O
Cl
N2 CHCOPh N
COPh
O
O
56102 Practical highly enantioselective synthesis of terminal propargylamines. An expeditious synthesisof (S)-(+)-coniineN. Gommermann, P. Knochel*, Chem. Commun., 2004, (20), 2324-2325
(i) CuBr, (R)-Quinaptoluene, rt, 3 d
(ii) TBAF
15 examples (7297% yield, 8498% ee) 84% yield, 98% ee
i-PrH
NBn2
i-PrCHO H SiMe3 HNBn2
(R)-Quinap =
N
PPh2
56103 First asymmetric SmI2-induced cross-coupling of Cr(CO)3 aromatic nitrone complexes with carbonylcompoundsM. Chavarot, M. Rivard, F. Rose-Munch*, E. Rose, S. Py, Chem. Commun., 2004, (20), 2330-2331
THF, 78 C, 30 min
6 examples (yield 6596%, dr >95 : 5) 96% yield, >95 : 5 dr
SmI2
Me
Cr(CO)3
NH
BnO
But H
O
Me
Cr(CO)3
NOH
Bn tBu
OHH
56104 An active ferrocenyl triarylphosphine for palladium-catalyzed SuzukiMiyaura cross-coupling of arylhalidesF. Y. Kwong*, K. S. Chan, C. H. Yeung, A. S. C. Chan*, Chem. Commun., 2004, (20), 2336-2337
Pd2(dba)3, LKF, THF, N2, rt, 24 h
17 examples (8398%) 98%MeO Br
OMe
B(OH)2 MeO
OMeL =
PPh2
Fe
6 METHODS IN ORGANIC SYNTHESIS January 2005
Chemical Communications
56105 A novel strategy for the preparation of arylhydroxylamines: chemoselective reduction of aromatic nitrocompounds using bakers yeastF. Li, J. Cui*, X. Qian*, R. Zhang, Chem. Commun., 2004, (20), 2338-2339
baker's yeastphosphate buffer, glucose,
30 C, 1 h
10 examples (conversion 86100%,c : d = 70 : 30 to >98 : 2)
conversion 99%
NO2
CNCN CN
CN
NHOH NH2
CNCN
c>98
d2
::
56106 Polysulfones: solid organic catalysts for the chemoselective cleavage of methyl-substituted allyl ethersunder neutral conditionsD. Markovic, P. Steunenberg, M. Ekstrand, P. Vogel*, Chem. Commun., 2004, (21), 2444-2445
cyclohexane, 80 C
85%12 substrates (8596%)
OHOHO
OCH2C(Me)=CH2
OO
OHOHO
OH
OO
SO2 SO2Na
n
56107 BINOL catalyzed enatioselective addition of titanium phenylacetylide to aromatic ketonesP. G. Cozzi*, S. Alesi, Chem. Commun., 2004, (21), 2448-2449
BuLi, ClTi(OiPr)3, 30 C, 24 h
70%, 89% ee8 ketone substrates (2898%, 2890% ee)
(R,R)-BINOLPh
O
+HO
Ph
56108 L-Proline catalyzed asymmetric transfer aldol reaction between diacetone alcohol and aldehydesS. Chandrasekhar*, C. Narsihmulu, N. R. Reddy, S. S. Sultana, Chem. Commun., 2004, (21), 2450-2451
DMSO, rt, 4 h
86%, 71% ee10 substrates (4091%, 4896% ee)
L-ProlineH
O
+
O2N
diacetone alcohol
NO2
O OH
56109 The first tandem double palladium-catalyzed aminations: synthesis of dipyrido[1,2-a:3,2-d]imidazole andits benzo- and aza-analoguesK. T. J. Loones, B. U. W. Maes*, R. A. Dommisse, G. L. F. Lemiere, Chem. Commun., 2004, (21), 2466-2467
CsCO3, toluene, reflux, 17 h
96%6 substrates (8298%)
Pd(OAc)2, BINAP or XANTPHOS+
NN
I
Cl NH2 NN
N
56110 Aziridine sulfides and disulfides as catalysts for the enantioselective addition of diethylzinc to aldehydesA. L. Braga*, P. Milani, M. W. Paixao, G. Zeni, O. E. D. Rodrigues, E. F. Alves, Chem. Commun., 2004, (21), 2488-2489
Toluene, rt, 24 h
82%, 87% ee (S)5 catalysts (4282%, 37>99% ee)
+H
O
Et2Zn
OHSN
Ar
2
METHODS IN ORGANIC SYNTHESIS January 2005 7
Chemical Communications
56111 Enantioselective synthesis of allenyl carbinols by the CBS reduction in nitroethane: dramatic solventeffect for reactivity and enantioselectivityC.-M. Yu*, C. Kim, J.-H. Kweon, Chem. Commun., 2004, (21), 2494-2495
Catecholborane, 78 C, 1 h, CH3CH2NO
93%, 93% ee6 substrates (8695%, 92>99% ee)
O
PhH2CH2CMe
HO
PhH2CH2CMe
HN B
O
Me
Ph Ph
European Journal of Organic Chemistry
56112 Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynesT. Jin, S. Kamijo, Y. Yamamoto*, Eur. J. Org. Chem., 2004, (18), 3789-3791
DMFMeOH, 100 C, 12 h
83%12 alkynes (5595%)
CuIH + TMSN3
NN
NH
H
Helvetica Chimica Acta
56113 Chrial borate esters in asymmetric synthesis Part 2 Asymmetric borane reduction of prochiral ketones inthe presence of a chiral spiroborate esterD. Liu, Z. Shan*, Y. Zhou, Z. Wu, J. Qin, Helv. Chim. Acta, 2004, 87(9), 2310-2317
THF, 05 C, 2 h98%, 92% ee7 substrates (692% ee)
O OH
+ BH3THF
O
OB
O O
HN
56114 Versatile one-step one-pot direct aldol condensation promoted by MgI2H.-X. Wei*, K. Li, Q. Zhang, R. L. Jasoni, J. Hu, P. W. Pare*, Helv. Chim. Acta, 2004, 87(9), 2354-2358
CH2Cl2, rt, 30 min
98%12 examples (6098%)
O O
+ H
O OHMgI2, EtN(iPr)2
Journal of Organic Chemistry
56115 Highly regio- and stereoselective synthesis of polysubstituted cyclopropane compounds via thePd(0)-catalyzed couplingcyclization reaction of 2-(2,3-allenyl)malonates with organic halidesS. Ma*, N. Jiao, Q. Yang, Z. Zheng, J. Org. Chem., 2004, 69(19), 6463-6477
n-Bu4NBr, CH3CN, 16 h
93%, cis:trans 6:9415 examples (4998%)
Pd(PPh3)4+ PhI
n-C6H13CO2Me
CO2Me
Ph
MeO2C CO2Me
C6H13
Me
8 METHODS IN ORGANIC SYNTHESIS January 2005
Journal of Organic Chemistry
56116 A facile synthesis of C2,N3-disubstituted-4-quinazoloneS. Xue*, J. McKenna*, W.-C. Shieh, O. Repic, J. Org. Chem., 2004, 69(19), 6474-6477
CH3CN,70 C
95%24 examples (8798%)
PCl3+
O
O
OH
O
NH
OO
O
Cl
NH2
O
O
N
O
NO
O
Cl
56117 Formation of a quaternary carbon center throught the Pd(0)/PhCOOH-catalyzed allylation of cyclic -ketoesters and 1,3-diketones with alkynesN. T. Patil, Y. Yamamoto*, J. Org. Chem., 2004, 69(19), 6478-6481
Toluene
98%14 examples (5198%)
Pd(0)/PhCOOH+
O
OEt
OCl
O OOEt
Cl
56118 Unexpected formation of tetrasubstituted 2,3-dihydrofurans from the reactions of -ketopolyfluoroalkanesulfones with aldehydesC. Xing, S. Zhu*, J. Org. Chem., 2004, 69(19), 6486-6488
Toluene, reflux, 1 hr
90%23 examples (7295%)
Piperidine+Cl(F2C)4O2S Ph
O
Br
O
H
O Ph
SO2(CF2)4Cl
O
Ph
Br
56119 Solvent free amination reactions of aryl bromides at room temperature catalyzed by a (-allyl)palladiumcomplex bearing a diphosphinidenecyclobutene ligandA. S. Gajare, K. Toyota, M. Yoshifuji*, F. Ozawa, J. Org. Chem., 2004, 69(19), 6504-6506
rt, 12 h
98%21 examples (6098%)
tBuOK, [Pd]+Ph Br Ph NH2 Ph
HN Ph
Ph
Ph
P
P
Mes*
Mes*
Pd
+ OTf-
[Pd] =
56120 Enantioselective cyanation/Brook rearrangement/C-acylation reactions of acylsilanes catalyzed by chiralmetal alkoxidesD. A. Nicewicz, C. M. Yates, J. S. Johnson*, J. Org. Chem., 2004, 69(20), 6548-6555
toluene, 45 C, 72 h
catalystcatalyst =
10 examples (7082% yield, 6182% ee) 81% yield, 78% ee
SiEt3
O
NC OBn
O
F
CO2Bn
F
NC OSiEt3
NNAl
OO ClClOiPr
56121 Arylboronic acids and arylpinacolboronate esters in Suzuki coupling reactions involving indoles. Partnerrole swapping and heterocycle protectionM. Prieto, E. Zurita, E. Rosa, L. Munoz, P. Lloyd-Williams*, E. Giralt*, J. Org. Chem., 2004, 69(20), 6812-6820
tolueneEtOHH2O, reflux
Pd(PPh3)4
34 examples (up to 99%) 85%NH
BrMeO
B(OH)2NH
MeO
Na2CO3
METHODS IN ORGANIC SYNTHESIS January 2005 9
Journal of Organic Chemistry
56122 Base-catalyzed endo-mode cyclization of allenes: easy preparation of five- to nine-membered oxacyclesC. Mukai*, M. Ohta, H. Yamashita, S. Kitagaki, J. Org. Chem., 2004, 69(20), 6867-6873
tBuOH, 30 C
tBuOK
7 examples (7198%) 94%HO
OTBDMS
OH
PO
OEtOEt
OPOEt
OEt
O
2. PPTS
1. (EtO)2PCl, Et3N
56123 Alkyl- or arylthiolation of aryl iodide via cleavage of the SS bond of disulfide compound by nickelcatalyst and zincN. Taniguchi*, J. Org. Chem., 2004, 69(20), 6904-6906
DMF, 100 C, 48 h
NiBr2-bpy, Zn
16 examples (6192%) 76%
I
SS
S
56124 The first conversion of primary alkyl halides to nitroalkanes under aqueous mediumR. Ballini*, L. Barboni, G. Carlo, J. Org. Chem., 2004, 69(20), 6907-6908
H2O, rt, 1 hAgNO2
13 examples (5390%) 83%I NO2
56125 Reactions on a solid surface. A simple, economical and efficient FriedelCrafts acylation reaction overzinc oxide (ZnO) as a new catalystM. H. Sarvari, H. Sharghi*, J. Org. Chem., 2004, 69(20), 6953-6956
The ZnO could be reused 3 times with little loss in activity
no solvent, rt, 10 minZnO
14 examples (5098%) 94%O
Cl Ph
O OPh
O
Journal of the American Chemical Society
56126 Bifunctional nanocrystalline MgO for chiral epoxy ketones via ClaisenSchmidt condensationasymmetricepoxidation reactionsB. Choudary*, M. Kantam, K. Ranganath, K. Mahendar, B. Sreedhar, J. Am. Chem. Soc., 2004, 126(11), 3396-3397
i) toluene, 100 Cii) TBHP, 25 C
10 examples(070% yield098% ee)
70% yield90% ee
NAP-MgOO
+
O
CH3Ph HPh Ph Ph
OO
56127 PtCl2-catalyzed cycloisomerizations of allenynesN. Cadran, K. Cariou, G. Herve, C. Aubert, L. Fensterbank, M. Malcria*, J. Marco-Contelles, J. Am. Chem. Soc., 2004,126(11), 3408-3409
PhMe, rt, 2448 h
12 examples(3290% yield)
75% yield
(5 mol%) PtCl2
H
MeO
MeOCH3
CH3H
HH
MeO
MeO
10 METHODS IN ORGANIC SYNTHESIS January 2005
Journal of the American Chemical Society
56128 Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed CN bondformationring-expansion processA. Klapars, S. Parris, K. Anderson, S. Buchwald*, J. Am. Chem. Soc., 2004, 126(11), 3529-3533
N,N-dimethylethylenediamine, K2CO3; PhMe, 110 C, 2224 h
12 examples(098% yield)
92% yield
(5 mol%) CuI+
NH2
INH
O
NH
HN
O
56129 Bronsted acid-promoted cyclizations of siloxyalkynes with arenes and alkynesL. Zhang, S. A. Kozmin*, J. Am. Chem. Soc., 2004, 126(33), 10204-10205
CH2Cl2, 20 C
92%11 examples (7699%)
HNTf2
OTIPS OTIPS
56130 Catalytic deallylation of allyl- and diallylmalonatesD. Necas, M. Tursky, M. Kotora*, J. Am. Chem. Soc., 2004, 126(33), 10222-10223
H+
99%16 examples (6899%)
EtAl3, NiBr2(PPh3)2EtOOC PhEtOOC
EtOOCPh
EtOOC
56131 Catalytic cross-coupling of alkylzinc halides with -chloroketonesC. F. Malosh, J. M. Ready*, J. Am. Chem. Soc., 2004, 126(33), 10240-10241
THFEt2O
95%22 examples (7096%)
Cu(acac)2, ZnCl2O
Cl+ iPrMgCl
OiPr
56132 Palladium-catalyzed cyclization/carboalkyation of alkenyl indolesC. Liu, R. A. Widenhoefer*, J. Am. Chem. Soc., 2004, 126(33), 10250-10251
MeOH, rt, 0.5 h
83%15 examples (4592%)
PdCl2(CH3CN)2, CuCl2HN
HN
MeO2C
56133 Ruthenium catalyzed [3 + 2] intramolecular cycloaddition of alk-5-ynylidenecyclopropanes promoted bythe first-generation Grubbs carbene complexF. Lopez, A. Delgado, J. R. Rodriguez, L. Castedo, J. L. Mascarenas*, J. Am. Chem. Soc., 2004, 126(33), 10262-10263
toluene, 110 C, 45 min
78%6 examples (5678%)
EtO2CEtO2C
EtO2CEtO2C
PCy3RuPCy3
Ph
ClCl
METHODS IN ORGANIC SYNTHESIS January 2005 11
Journal of the American Chemical Society
56134 Alkylation of alkenes: ethylaluminium sesquichloride-mediated hydro-alkyl additions with alkylchloroformates and di-tert-butylpyrocarbonateU. Biermann, J. O. Metzger*, J. Am. Chem. Soc., 2004, 126(33), 10319-10330
CH2CL2, 15 C, 1 h
82%33 examples (3084%)
Et3Al2Cl3iPr
O Cl
O+
56135 Self-supported heterogenous catalysts for enantioselective hydrogenationX. Wang, K. Ding, J. Am. Chem. Soc., 2004, 126(34), 10524-10525
toluene, H2, 4 atm, 25 C, 10 h
4 examples(>99% conversion89.597.3% ee)
>99% conversion95% ee
(1 mol%) catalystH OCH3
NHAc
O
HCO2CH3
NHAc
catalyst =O
OP
[Rh]N O
OP
NLinker
n
56136 Regio- and chemoselective direct generation of functionalized aromatic aluminium compounds usingaluminium ate baseM. Uchiyama*, H. Naka, Y. Matsumoto, T. Ohwada, J. Am. Chem. Soc., 2004, 126(34), 10526-10527
ii) I213 examples
(40100% yield) 99% yield
i) iBu3Al(TMP)L, THF, 78 Crt, 112 h
OMe OMeI
56137 Nickel-catalyzed intermolecular [3 + 2 + 2] cocyclization of ethyl cyclopropylideneacetate and alkynesS. Saito*, M. Masuda, S. Komagawa, J. Am. Chem. Soc., 2004, 126(34), 10540-10541
toluene, Ar, rt, one night9 examples
(2589% yield)
(10 mol%) Ni(cod)2(20 mol%) PPh3
COOEt
+ Ph H
COOEt
Ph
HPh
H
56138 Intramolecular CN bond addition of amides to alkynes using platinum catalystT. Shimada, I. Nakamura, Y. Yomamoto*, J. Am. Chem. Soc., 2004, 126(34), 10546-10547
anisole, 80100 C, 0.324 h
14 examples(0>99% yield)
(5 mol%) PtCl2+
94% yield
Ph
N Me
O
MeN
Me
PhO
MeN
Me
H
Me
56139 Hydroxyapatite-supported palladium nanoclusters: a highly active heterogenous catalyst for selectiveoxidation of alcohols by use of molecular oxygenK. Mori, T. Hara, T. Mizugaki, K. Ebitani, K. Kaneda*, J. Am. Chem. Soc., 2004, 126(34), 10657-10666
trifluorotoluene, O2 atm, 90 C, 124 h
Numerous examples(8499% conversion
8099% yield)
(0.1 g) PhHAP-0
97% conversion94% yield
O
O
OH O
O
CHO
12 METHODS IN ORGANIC SYNTHESIS January 2005
Journal of the American Chemical Society
56140 Cu-catalyzed asymmetric allylic alkylations of aromatic and aliphatic phosphates with alkylzinc reagents.An effective method for enantioselective synthesis of tertiary and quaternary carbonsM. Kacprzynski, A. Hoveyda*, J. Am. Chem. Soc., 2004, 126(34), 10676-10681
Et2Zn, THF, 15 C, N2 atm, 24 h
22 examples(5895% yield7896% ee)
90% yield91% ee
(10 mol%) chiral Schiff base(5 mol%) (CuOTf)2C6H6OPO(OEt)2H5C6
H5C6
56141 Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenesM. R. Luzung, J. P. Markham, F. D. Toste*, J. Am. Chem. Soc., 2004, 126(35), 10858-10859
(Ph3P)AuPF6CH2Cl2, rt
10 examples (6199%) 99%
Ph
Ph
H
H
56142 Highly diastereoselective and enantioselective CH functionalization of 1,2-dihydronaphthalenes: acombined CH activation/Cope rearrangement followed by a retro-Cope rearrangementH. M. L. Davies*, Q. Jin, J. Am. Chem. Soc., 2004, 126(35), 10862-10863
2,2-dimethylbutane, 0 C
13 examples(yield 5395%, de >98%, ee 9199%) 95% yield, >98% de, 99.5% ee
Rh2(S-DOSP)4N2
Ph
CO2Me
Ph
HCO2Me
Rh2(S-DOSP)4 =
NSO2Ar
O
O
Rh
Rh
H
4
56143 Bidentate NHC-based chiral ligands for efficient Cu-catalyzed enantioselective allylic alkylations:structure and activity of an air-stable chiral Cu complexA. O. Larsen, W. Leu, C. N. Oberhuber, J. E. Campbell, A. H. Hoveyda*, J. Am. Chem. Soc., 2004, 126(36), 11130-11131
N
Me2Zn, TFH, 15 C, 24 h
>98% conversion, 74% ee15 examples
(4294% yield, 7198% ee)
[Ag], (CuOTf)2.C6H6Ph OPO(OEt)2
H
Ph
HMe
OAg
N
AgO
NN
[Ag] =
56144 Chemoslective silylzincation of functionalized terminal alkynes using dianion-type zincate(SiBNOL-Zn-ate): regiocontrolled synthesis of vinylsilanesS. Nakamura, M. Uchiyama*, T. Ohwada, J. Am. Chem. Soc., 2004, 126(36), 11146-11147
THF, rt, 12 h
100%16 examples (73100%)
[Zn][Zn] =H
PhH
HSi
Ph
MeMe
Me OO
ZnSi
tBu
MeMe
Me
56145 Catalytic enantioselective Michael addition of 1,3-dicarbonyl compounds to nitroalkenes catalyzed bywell-defined chiral Ru amido complexesM. Watanabe, A. Ikagawa, H. Wang, K. Murata, T. Ikariya*, J. Am. Chem. Soc., 2004, 126(36), 11148-11489
Toluene, 20 C, 48 h
99%, 95% ee18 examples (599%, 3098% ee)
[Ru][Ru] =Ph
NO2 + CH2(CO2CH3)2Ph
NO2CH(CO2CH3)2
NH
RuNC6H5
C6H5
SO O
METHODS IN ORGANIC SYNTHESIS January 2005 13
Journal of the American Chemical Society
56146 AuCl3-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-onesT. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc., 2004, 126(36), 11164-11165
CH2Cl2, rt, 1 h
88%12 examples (5290%)
AuCl3+ MeOH
O Ph OPh
OMe
56147 Zirconium-catalyzed enantioselective [3+2] cycloaddition of hydrazones to olefins leading to opticallyactive pyrazolidine, pyrazoline and 1,3-diamine derivativesY. Yamashita, S. Kobayashi*, J. Am. Chem. Soc., 2004, 126(36), 11279-11282
Toluene, 0 C, 18 h
94%22 examples (6795%, 4298% ee)
Zr(OPr)4, [L]+N
PhH2CH2C H
NH
O C6H4(p-NO2)
OEt HN NC6H4(p-NO2)
O
PhH2CH2C OEt
I I
II
OMe[L] =
56148 Highly enantioselective conjugate addition of nitroalkanes to alkylidenemalonates using efficientphase-transfer catalysis of N-spiro chiral ammonium bromidesT. Ooi, S. Fujioka, K. Maruoka*, J. Am. Chem. Soc., 2004, 126(38), 11790-11791
Toluene, 0 C
99%, 98% ee9 examples (9799%, 8899% ee)
Cs2CO3, [N]Et NO2
CO2iPr
CO2iPrF
CO2iPr
CO2iPrF
EtO2NN
Ar
ArBr
F3C CF3
CF3
CF3
Ar =
+
[N] =
56149 Organocatalytic asymmetric aza-FriedelCrafts alkylation of furanD. Uraguchi, K. Sorimachi, M. Terada*, J. Am. Chem. Soc., 2004, 126(38), 11804-11805
1,2-dichloroethane, 35 C, 24 h95%, 96% ee13 substrates (8496%, 8697% ee) Ar = 3,5-dimesityl phenyl
+OMeO N
p-MeO-C6H4H
BocOMeO
p-MeO-C6H4
NHBoc
Ar
OO
Ar
PO
OH
56150 Gold-catalyzed cycloisomerization of siloxy enynes to cyclohexadienesL. Zhang, S. A. Kozmin*, J. Am. Chem. Soc., 2004, 126(38), 11806-11807
20 C, CH2Cl2
99%8 substrates (5099%)
Ph Me
OTIPS
AuCl Ph
TIPSO
Me
14 METHODS IN ORGANIC SYNTHESIS January 2005
Organic Letters
56151 New entries in Lewis acidLewis base bifunctional asymmetric catalyst: catalytic enantioselectiveReissert reaction of pyridine derviativesE. Ichikawa, M. Suzuki, K. Yabu, M. Albert, M. Kanai*, M. Shibasaki*, J. Am. Chem. Soc., 2004, 126(38), 11808-11809
CH2Cl2, 60 C, 27 h
98%, 91% ee7 substrates (8598%, 57>99%)
Et2AlCl, [L]
N
NMe2
O
+ TMSCN + MeOCOCl
N
NMe2
O
NC
OHOH
S
S
O
Ph
O
Ph
[L] =
New Journal of Chemistry
56152 Copper promoted synthesis of diaryl ethersR. Ghosh, A. G. Samuelson*, New J. Chem., 2004, 28(11), 1390-1393
K3PO4, THF, 18 h
33 examples (7>99%) >99%
CuCO3Cu(OH)2H2O
ONa Br
CN
O
CN
Organic & Biomolecular Chemistry
56153 Bromine catalyzed conversion of S-tert-butyl groups into versatile and, for self-assembly processesaccessible, acetyl-protected thiolsA. Blaszczyk, M. Elbing, M. Mayor*, Org. Biomol. Chem., 2004, 2(19), 2722-2724
AcCl/AcOH, rt
94%9 substrates (2997%)
Br2Br S Br S
O
56154 The first Cu(I)-mediated nucleophilic trifluoromethylation reactions using (trifluoromethyl)trimethylsilanein ionic liquidsJ. Kim, J. M. Shreeve*, Org. Biomol. Chem., 2004, 2(19), 2728-2734
[IL], 25 C, 3 h
88%8 examples (8898%)
CsF, TMSCF3O
H
OH
HCF3 NOO
O
N(SO2CF3)[IL] =
Organic Letters
56155 Improved procedure for the oxidative cleavage of olefins by OsO4NaIO4W. Yu, Y. Mei, Y. Kang, Z. Hua, Z. Jin*, Org. Lett., 2004, 6(19), 3217-3219
Use of 2,6-lutidine dramatically improved the yield of aldehyde (from 2144% for the same 5 examples)
dioxanewater, 25 C, 20 h
OsO4, NaIO4, 2,6-lutidine
5 examples (7199%) 99%
OO
OTBS
OO
CHO
OTBS
METHODS IN ORGANIC SYNTHESIS January 2005 15
Organic Letters
56156 Titanium catalysis in the Ugi reaction of -amino acids with aromatic aldehydesT. Godet, Y. Bovin, G. Vincent, D. Merle, A. Thozet, M. A. Ciufolini*, Org. Lett., 2004, 6(19), 3281-3284
MeOH, rt, 12 h
TiCl4
16 amino acid and aryl aldehyde examples (7592%, 1.510 : 1 dr) 79%, 5 : 1 dr at *
HOCO2H
NH2
HOMeO2C
NH
CONHtBu
OMeMeOOMeMeO
OHCNtBuC
*
56157 Copper-mediated cross-coupling reactions of N-unsubstituted sulfoximines and aryl halidesG. Y. Cho, P. Remy, J. Jansson, C. Moessner, C. Bolm*, Org. Lett., 2004, 6(19), 3293-3296
DMSO, 90 C
CuI
18 examples (4895%) 72%
IOMe
PhSNH
MeO Cs2CO3 OMe
PhSN
MeO
56158 A highly diastereoselective MgI2-mediated ring expansion of methylenecyclopropanesM. E. Scott, W. Han, M. Lautens*, Org. Lett., 2004, 6(19), 3309-3312
THF, reflux, 16 h
MgI2
13 examples (6594%, only one isomer observed in all but 2 examples) 82%, one isomer
SN
O
N
SN
O
N ONPh2
O
NPh2
56159 Asymmetric transfer hydrogenation in water with a supported NoyoriIkariya catalystX. Li, X. Wu, W. Chen, F. E. Hancock, F. King, J. Xiao*, Org. Lett., 2004, 6(19), 3321-3324
The catalyst could be reused more than 10 times with no loss in enantioselectivity
water, 22 C, 18 h
Ru-PTsDPEN
16 examples (>87% yield, 8594% ee) 87% yield, 91% ee
OO
OOH
Ru-PTsDPEN =
NTsRu
H2N
O O
Cl
HCO2Na
56160 Palladium-catalyzed dimerization disilylation of 1,3-butadiene with chlorosilanesJ. Terao, A. Oda, N. Kambe*, Org. Lett., 2004, 6(19), 3341-3344
THF, 20 C
Pd(acac)2
7 examples (5793%, >78 : 22 E : Z) 88%, E isomer only
Ph Si Cl SiMe2PhSiMe2Ph
PhMgBr
56161 Organic reactions in water: an efficient zinc-mediated stereoselective synthesis of (E)- and(Z)-trisubstituted alkenes using unactivated alkyl halidesB. Das*, J. Banerjee, G. Mahender, A. Majhi, Org. Lett., 2004, 6(19), 3349-3352
Zn, sat. aq. NH4Cl
21 examples (5886%, Z : E >80 : 20 for X = CN, 0 : 100 for X = CO2Me)
OAcX I
X
X = CNX = CO2Me
rt, 12 hrt, 10 h
80%, 94 : 6 Z : E84%, 0 : 100 Z : E
16 METHODS IN ORGANIC SYNTHESIS January 2005
Organic Letters
56162 Chemoselective cyclizations of divinyl ketones to cyclohexenones mediated by Lewis acid and baseN. A. Magomedov*, P. L. Ruggiero, Y. Tang, Org. Lett., 2004, 6(19), 3373-3375
toluene, 23 C
2,6-di-t-butylphenol,Me3Al, Et3N
6 examples (7492%) 91%
O
SO2Ph
OSO2Ph
56163 ROMPgel-supported thiazolium iodide: an efficient supported organic catalyst for parallel Stetter reactionsA. G. M. Barrett*, A. C. Love, L. Tedeschi, Org. Lett., 2004, 6(19), 3377-3380
DMF, 80 C, 20 h
catalystcatalyst =
15 examples (6899% yield, >66% purity) 95% yield, >95% purity
O OO Ph
N
Sn
INEt3
OHC
56164 Catalytic enantioselective conjugate addition of trimethylsilylacetylene to 2-cyclohexen-1-oneY.-S. Kwak, E. J. Corey*, Org. Lett., 2004, 6(19), 3385-3388
tBuOMe, 0 C, 45 min O ONi
catalyst =
86% yield8288% ee
O
Me2Al SiMe3
O
SiMe3
NN
O OCN
Ph Ph
catalyst
56165 Highly enantioselective dimerization of ,-enones catalyzed by a rigid quaternary ammonium saltF.-Y. Zhang, E. J. Corey*, Org. Lett., 2004, 6(19), 3397-3399
The products could be converted to -chiral -keto acids by treatment with ozone, followed by hydrogen peroxide
50% aq. KOH,toluene, 40 C, 12 h
catalystcatalyst =
7 examples (7981% yield, 8398% ee) 89% yield, 90% eeF
O
F
O O
FN
NH
H
HOH
Br
56166 A 1,3-diaza-Claisen rearrangement that affords guanidinesA. M. Bowser, J. S. Madalengoitia*, Org. Lett., 2004, 6(19), 3409-3412
CHCl3, rt
EDCIEDCI =
7 examples (6685%) 72%
N
Ph
N NN
C HClTs
NH
NH
SN
N
NTs
PhH
H
56167 Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition ofarylboronic acids to fumaric and maleic compoundsR. Shintani, K. Ueyama, I. Yamada, T. Hayashi*, Org. Lett., 2004, 6(19), 3425-3427
dioxaneH2O, 50 C, 3 h
[RhCl(C2H4)2]2, ligand ligand =
8 examples (7795% yield, 6992% ee) 88% yield, 85% ee
N
O
OF
B(OH)2N
O
OF
METHODS IN ORGANIC SYNTHESIS January 2005 17
Organic Letters
56168 Azadiene DielsAlder cycloaddition of fulvenes: a facile approach to the [1]pyrindine systemB. Hong*, J. Wu, A. Gupta, M. Hallur, J. Liao, Org. Lett., 2004, 6(20), 3453-3456
ClC6H5, microwave, 125 C, 0.337 h
9 examples(2996% yield)
87% yield
+
CO2Et
NSO2Ph N
H
H
CO2Et
SO2Ph
56169 Regioselective cross-metathesis reaction induced by steric hindranceS. BouzBouz*, R. Simmons, J. Cossy*, Org. Lett., 2004, 6(20), 3465-3467
CH2Cl2, 40 C14 examples
(2383% yield)80% yield
+(5 mol%) Ru catalyst
OTBDPS
OMe
OOMe
O
OTBDPS
56170 One-pot homolytic aromatic substitutions/HWE olefinations under microwave conditions for the formationof a small oxindole libraryA. Teichert, K. Jantos, K. Harms, A. Studer*, Org. Lett., 2004, 6(20), 3477-3480
2) microwave, 6 min, KOt-Bu, PhCHO
13 examples(3587% yield)
75% yield
1) microwave, 2 min, DMF, 180 C, 0.03 MN
PEtO
O
OEtO
N
O
N
OPh
56171 Highly regioselective synthesis of tetrahydro-2H-1,3-thiazin-2-ones via rhodium-catalyzed carbonylationof N-alkylisothiazolidinesC. Dong, H. Alper*, Org. Lett., 2004, 6(20), 3489-3492
(0.05 mmol) KI, toluene, CO (1000 psi), 24 h9 examples
(3585% yield) 75% yield
(0.05 mmol) [Rh(COD)Cl]2
HS
N n N
S O H
n
56172 2-C-branched glycosides from 2-carbonylalkyl 2-O-Ms(Ts)-C-glycosides. A tandem SN2SN2 reaction via1,2-cyclopropanated sugarsH. Shao, S. Ekthawatchai, S. Wu, W. Zou*, Org. Lett., 2004, 6(20), 3497-3499
K2CO3/MeOH, rt, overnight13 examples
(5085% yield) 81% yield
MeOHO
BnOBnO
BnO
Me
O
OMsO
BnOBnO
BnO
Me
O
56173 Cp*Ir complex catalyzed N-heterocyclization of primary amines with diols: a new catalytic system forenvironmentally benign synthesis of cyclic aminesK. Fujita*, T. Fujii, R. Yamaguchi*, Org. Lett., 2004, 6(20), 3525-3528
NaHCO3, toluene, 110 C, 17 h14 examples
(6394% yield) 91% yield
[Cp*IrCl2]2NH2 + HO OH N
18 METHODS IN ORGANIC SYNTHESIS January 2005
Organic Letters
56174 Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylationA. Alexakis*, D. Polet, Org. Lett., 2004, 6(20), 3529-3532
NaHC(CO2Me)2, THF, 2565 C, 266 h20 examples
(2199% yield1098% ee) 90% yield97% ee
[IrCODCl]2ligandOCO2Me
Cl
CH(CO2Me)2
+Cl
Cl
CH(CO2Me)2OO
P N
Me
Me
ligand =(6 examples)
56175 Synthesis and trimethylaluminum additions on -hydroxy--sulfinyl and sulfonyl enoatesM. Carreno*, M. Sanz-Cuesta, F. Colobert*, G. Solladie*, Org. Lett., 2004, 6(20), 3537-3540
CH2Cl2, 17 h, 0 C4 examples
(9098% yield) 90% yield
AlMe3p-Tol
EtO
O
OH O
p-Tol
OOH
OHMeMe
56176 Palladium-catalyzed benzylation of active methine compounds without additional base: remarkableeffect of 1,5-cyclooctadieneR. Kuwano*, Y. Kondo, Org. Lett., 2004, 6(20), 3545-3547
THF, 80 C, 372 h23 examples
(71>99% yield) 84% yield
Cp(3-C3H5)PdDPPF
HOCOMe
O +H C CO2Et
CO2Et
Ph H CO2Et
CO2Et
Ph
56177 Synthesis of a new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzedasymmetric hydrogenation reactionsS. Wu, W. Zhang, Z. Zhang, X. Zhang*, Org. Lett., 2004, 6(20), 3565-3567
H2 (25 psi)8 examples
(99.799.9% ee) 98.2% ee
(0.001 mmol) [Rh(nbd)2]BF4-ligandCOOCH3
NHAcH
COOCH3
NHAcH*
56178 Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: a new class of practical ligands forRh-catalyzed asymmetric hydrogenationX. Hu, Z. Zheng*, Org. Lett., 2004, 6(20), 3585-3588
CH2Cl2, H2 (10 bar), rt, 0.51 h7 examples
(10.699% ee) 99.6% ee
Rh(COD)2BF4-ligand
H
HN
O
H
HN
O
*
ligand =(6 examples)
O
OPN
PPh2
Fe
56179 Novel [2 + 2 + 2 + 1] cycloaddition of enediynes catalyzed by rhodium complexesB. Bennacer, M. Fujiwara, I. Ojima*, Org. Lett., 2004, 6(20), 3589-3591
Cl(CH2)2Cl/toluene, CO (1 atm) 5080 C, 2136 h
8 examples(1193% yield) 87% yield
(5 mol%) [Rh(COD)Cl]2OMeOMeMeO
MeO
O
MeOMeO
OMeOMe
METHODS IN ORGANIC SYNTHESIS January 2005 19
Organic Letters
56180 A new ketone synthesis by palladium-catalyzed cross-coupling reactions of esters with organoboroncompoundsH. Tatamidani, F. Kakiuchi, N. Chatani*, Org. Lett., 2004, 6(20), 3597-3599
dioxane, 50 C, 10 h14 examples
(1697% yield)89% yield
(0.03 mmol) Pd(OAc)2(0.09 mmol) PPh3OPy
ClO
Ph
OCl
56181 Highly enantioselective asymmetric hydrogenation of -acetamido dehydroamino acid derivatives using athree-hindered quadrant rhodium catalystH. Wu, G. Hoge*, Org. Lett., 2004, 6(20), 3645-3647
solvent, H2 (650 psi), THF/MeOH, EtOAc
7 examples(6699% ee)
96% ee
(1 mol%) Rh catalystCO2Et
NHAcPr
CO2Et
NHAcPr
56182 Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines,tetrahydro[1,8]napthyridines, and tetrahydro-5H-pyrido[2,3-b]azepin-8-onesE. Bacque, M. El Qacemi, S. Zard*, Org. Lett., 2004, 6(21), 3671-3674
lauroyl peroxide, 1,2-dichloroethane,
Numerous examples3799% yield
R S O
SN NCln
Olauroyl peroxide, chlorobenzeneN NCl
n
O
SR
EtOS
N NClO
Rn
56183 Highly efficient stereoconservative amidation and deamidation of -amino acidsD. Shendage, R. Frolich, G. Haufe*, Org. Lett., 2004, 6(21), 3675-3678
ii) 1,4-dioxane, reflux, 5 h13 examples(098% yield)
96% yield
i) NaNO2, Ac2OAcOH (2 : 1),
04 C, 1416 hPhtN
NHMe
O
Me
PhtNOMe
O
Me
56184 Mercuric triflate-catalyzed synthesis of 2-methylfurans from 1-alkyn-5-onesH. Imagawa, T. Kurisaki, M. Nishizawa*, Org. Lett., 2004, 6(21), 3679-3681
C6H6, 0.520 h, rt9 examples
(099% yield)98% yield
(5 mol%) Hg(OTf)2O O
56185 Stereoselective synthesis of multisubstituted butadienes through directed MizorokiHeck reaction andhomocoupling reaction of vinyl(2-pyridyl)silaneK. Itami*, Y. Ushiogi, T. Nokami, Y. Ohashi, J. Yoshida*, Org. Lett., 2004, 6(21), 3695-3698
CH3CN, rt, 3 h15 examples
(24>99% yield) 70% yield
(11.2 equiv) CuI(1.31.5 equiv) CsF
SiMe2Py
S S
S
20 METHODS IN ORGANIC SYNTHESIS January 2005
Organic Letters
56186 Racemic but tropos (chirally flexible) BIPHEP ligands for Rh(I)-complexes: highly enantioselectiveene-type cyclization of 1,6-enynesK. Mikami*, S. Kataoka, Y. Yusa, K. Aikawa, Org. Lett., 2004, 6(21), 3699-3701
(20 mol%) TfOH, (CH2Cl2)2, 525 C, 0.519 h
5 examples(2099% yield5694% ee)
84% yield88% ee
(10 mol%) catalyst
Cl
O
Me
ClMe
O
*
N
NH2
H2
PPh2
PRh+
Ph2
Catalyst =
56187 Preparation of tertiary amides from carbamoyl chlorides and organocupratesL. Lemoucheux, T. Seitz, J. Rouden*, M. Lasne, Org. Lett., 2004, 6(21), 3703-3706
THF/Et2O, 300 C, 2 h19 examples
(3090% yield) 85% yield
(t-Bu)2CuLiLiCNN Cl
O
Nt-Bu
O
56188 Ring-closing metathesis of 2,2-divinylbiphenyls: a novel and general approach to phenanthrenesA. Luliano*, P. Piccioli, D. Fabbri, Org. Lett., 2004, 6(21), 3711-3714
CH2Cl2/toluene, 25110 C, 224 h
5 examples(0100% yield) 100% yield
(10 mol%) catalyst
H3CO
Catalyst (2 examples)OCH3
N N
RuPCy3Cl
Cl
56189 Cp2Fe(PR2)2PdCl2 (R = i-Pr, t-Bu) complexes as air-stable catalysts for challenging Suzuki couplingreactionsT. Colacot*, H. Shea, Org. Lett., 2004, 6(21), 3731-3734
EtOHH2O, K2CO3,12 h, 80 C
12 examples(0100% yield)
93% yield
(0.01 eq.) catalystCatalyst (7 examples)
FBr
MeO
PhB(OH)2 + FPh
MeO
PPd
Pt-Bu2
Cl
Clt-Bu2
56190 Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenolswith silylaryl triflatesZ. Liu, R. Larock*, Org. Lett., 2004, 6(21), 3739-3741
MeCN, CsF, 100 C, 24 h
10 examples(6687% yield)
85% yield
(10 mol%) PCy3(5 mol%) Pd(OAc)2
OH
IMeO2C O
MeO2C
METHODS IN ORGANIC SYNTHESIS January 2005 21
Organic Letters
56191 An efficient synthesis of -C-glycosides based on the conformational restriction strategy: Lewis acidpromoted silane reduction of the anomeric position with complete stereoselectivityM. Terauchi, H. Abe, A. Matsuda, S. Shuto*, Org. Lett., 2004, 6(21), 3751-3754
CH2Cl2, 78 C, 60 min
13 examples(5395% yield)
90% yield
Et3SiH, TMSOTfOOBn
Ph
OHBnO
OO
MeO
OMe
OOBn
PhBnO
OO
MeO
OMe
56192 Regioselective enzymatic acylation of -L-2-deoxynucleosides: application in resolution of-D/L-2-deoxynucleosidesJ. Garcia, S. Fernandez, M. Ferrero, Y. Sanghvi, V. Gotor*, Org. Lett., 2004, 6(21), 3759-3762
THF, 30 C, 0.5192 h
4 examples(1495% yield
>99% ee)90% yield>99% ee
lipaseLevO
NO OHT
OH
+
O OLevT
OH
56193 Enantioselective aldol reaction of trimethoxysilyl enol ether catalyzed by lithium binaphtholateM. Nakajima*, Y. Orito, T. Ishizuka, S. Hashimoto, Org. Lett., 2004, 6(21), 3763-3765
H2O, THF, 23 C, 0.5 h
11 examples(7598% yield
897% ee (syn)095% ee (anti))
94% yield>97% ee (syn)84% ee (anti)
(10 mol%) catalyst
CHO
+
OSi(OMe)3 O OH catalyst =Br
OLiOLi
Br
56194 Efficient and selective removal of methoxy protecting groups in carbohydratesA. Boto*, D. Hernandez, R. Hernandez, E. Suarez, Org. Lett., 2004, 6(21), 3785-3788
(diacetoxyiodo)benzene, I2, CH2Cl2, 25 C, h (80 w)
7 examples(5190% yield)
82% yield
OMeO OH
OMeOMe
MeOO
O
OMeOMe
MeO+
O
OO OH
OMeOMe
MeO
AcO
56195 Environmentally benign synthesis of H-phosphonic acids using a water-tolerant, recyclablepolymer-supported catalystS. Deprele, J. Montchamp*, Org. Lett., 2004, 6(21), 3805-3808
H3PO2, CH3CN, N2, refluxrt, 312 h, 15 runs
12 examples(4292% yield)
91% yield
(0.5 mol%) Pd catalystCl Cl PO2H2 N ONH
O PPh2
PPh2
Pd
Catalyst =
22 METHODS IN ORGANIC SYNTHESIS January 2005
Synthesis
56196 Application of phosphineoxazoline ligands in Ir-catalyzed asymmetric hydrogenation of acyclic aromaticN-aryliminesA. Trifonova, J. Diesen, C. Chapman, P. Andersson*, Org. Lett., 2004, 6(21), 3825-3827
CH2Cl2, N2 (20 bar), rt
9 examples(099% conversion
6696% ee)98% conversion
90% ee
(0.5 mol%) catalyst
Catalyst (2 examples) =
MeO
N
MeO
HN
*
N
Ph
IrPh
O
N
i-PrH
56197 An ionic liquid-coordinated palladium complex: a highly efficient and recyclable catalyst for the HeckreactionJ. Xiao, B. Twamley, J. Shreeve*, Org. Lett., 2004, 6(21), 3845-3847
ionic liquid, NaCO3, 100 C, 4 h3 examples
(7094% yield)83% yield
(2 mol%) PdCl2Cl + Ph
Ph
56198 Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range ofacceptorsC. Defieber, J. Paquin, S. Serna, E. Carreira*, Org. Lett., 2004, 6(21), 3873-3876
KOH, dioxane/H2O, 118 h, 50 C16 examples
(4398% yield8898% ee)
93% yield88% ee
(1.5 mol%) [Rh(C2H4)2Cl]2+ PhB(OH)2MeO
O
MeO
O Ph
56199 Synthesis of seven-membered ring glycals via endo-selective alkynol cycloisomerizationE. Alcazar, J. Pletcher, F. McDonald*, Org. Lett., 2004, 6(21), 3877-3880
ii) Ac2O, DMAP
9 examples(1796% yield) 81% yield
i) (15%) W(CO)6, Et3N, THF,h (350 nm), 5570 C, 6 hO
OMe
Me
HOH
HOO
AcO
O O
Synthesis
56200 Iodine catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones: a simple and efficientprocedure for the Biginelli reactionK. V. N. S. Srinivas, B. Das*, Synthesis, 2004, (13), 2091-2093
CH3CN, reflux, 7 h
86%29 substrates (7293%)
I2
CH3
H
O
H3C OCH2CH3
O O+ +
H2N NH2
O
NH
NH
H3C
H3CH2CO
O
CH3
METHODS IN ORGANIC SYNTHESIS January 2005 23
Synthesis
56201 Simple and improved procedure for the regioselective acylation of aromatic ethers with carboxylic acidson the surface of graphite in the presence of methanesulfonic acidM. H. Sarvari, H. Sharghi*, Synthesis, 2004, (13), 2165-2168
010 C, 20 min
98%12 substrates (8098%)
GraphiteMeSO3H+ MeCO2H
OMe
MeO
O
Me
56202 An improved catalytic system, Pd(PPh3)4/PhCOOH combined catalyst, for the allylation of carbonpronucleophiles with allenesN. T. Patil, N. K. Pahadi, Y. Yamamoto*, Synthesis, 2004, (13), 2186-2190
1,4 dioxane, 100 C, 12 h90%10 examples (7090%)
Pd(PPh3)4, PhCOOH+C C CH2
H
Ph
COOEt
COOEt
PhCOOEt
COOEt
56203 A novel four-component reaction for the diastereoselective synthesis of some new spiro pyrrolizidinesvia 1,3-dipolar cycloaddition of azomethine ylidesJ. Azizian*, A. R. Karimi, A. A. Mohammadi, M. R. Mohammadizadeh, Synthesis, 2004, (14), 2263-2265
Reaction proceeds to 7686% yields under reflux for 23 h.
DMSO, 35 min
89%6 examples (8795%)
MW
+
O
O
OHOH
NH2
NH2
+
NH
CO2H
O
O
Cl
+
N
N
N N
O
O
Cl
H
H
+
56204 Highly efficient double-activation catalysts for the synthesis of ketone cyanohydrinsF.-X. Chen, X. Liu, B. Qin, H. Zhou, X. Feng*, G. Zhang, Synthesis, 2004, (14), 2266-2272
rt, 13 h
99%13 examples (8499%)
AlEt3, [L]+
O
N
ONC O Si
OH
N N
HO
[L] =
56205 Ionic liquids promoted multi-component reaction: green appraoch for highly substituted 2-aminofuranderivativesJ. S. Yadav*, B. V. S. Reddy, S. Shubashree, K. Sadashiv, J. J. Naidu, Synthesis, 2004, (14), 2376-2380
rt, 2 h
84%12 examples (7889%)
[bmim]BF4+
MeOOC
COOMe
H
O
+
NC
O NH
MeO2C CO2Me
56206 A new reactive system for HornerWadsworthEmmons olefination of optically active4-hydroxy-2-oxo-alkylphosphonates and 4-hydroxy-1-1chloro-2-oxo-alkylphosphonates with aliphaticaldehydesC. Xu, C. Yuan*, Synthesis, 2004, (15), 2449-2458
H2O, THF94%, >99% ee26 examples (7696%, 95>99% ee)
K2CO3+
PhP(OEt)2
OOH OEtCHO
Ph
OOH
Et
24 METHODS IN ORGANIC SYNTHESIS January 2005
Synthesis
56207 TFFH as an excellent reagent for acylation of alcohols, thiols and dithiocarbamatesM. Pittelkow, F. S. Kamounah, U. Boas, B. Pedersen, J. B. Christensen*, Synthesis, 2004, (15), 2485-2492
DMAP, rt, over night
97%20 examples (3897%)
TFFH+
OH
O
HO O
O
TFFH = N NF PF6
56208 Bi(OTf)3 as novel and efficient catalyst for the stereoselective synthesis of C-pseudoglycalsJ. S. Yadav*, B. V. S. Reddy, K. S. Reddy, L. Chandraiah, V. Sunitha, Synthesis, 2004, (15), 2523-2526
MeCN, rt, 15 min
95%10 examples (8795%)
Bi(OTf)3+
OAcO
OAcAcO
TMSOAcO
AcO
56209 Novel synthetic strategy of N-arylated heterocycles via sequential palladium-catalyzed intra- andinter-arylamination reactionsR. Omar-Amrani, R. Schneider*, Y. Fort*, Synthesis, 2004, (15), 2527-2534
NaH, tBuOH, 1,4-dioxane, 100 C, 8 h
92%19 examples (4199%)
Pd(OAc)2+
Cl
NH2Cl
N
56210 Facile synthesis of 2,3-disubstituted quinoxalines by SuzukiMiyaura couplingL. Mao, H. Sakurai*, T. Hirao*, Synthesis, 2004, (15), 2535-2539
K2CO3, tolueneethanol, reflux, 48 h
92%14 examples (7796%)
Pd(PPh3)4+ PhB(OH)2NN
Cl Cl
NN
Ph Ph
56211 The reaction of carbonyldiimidazole with alcohols to form carbamates and N-alkylimidazolesY. Tang, Y. Dong, J. L. Vennerstrom*, Synthesis, 2004, (15), 2540-2544
MeCN, rt, 2 h
100%28 examples (10100%)
Carbonyl diimidazoleO
O OH
O
O
OO
N
N
56212 Unexpected addition of methyl 3,3,3-trifluoropyruvate to push-pull enamines having a methyl group at-positionD. M. Volochnyuk, A. N. Kostyuk*, D. A. Sibgatulin, A. E. Petrenko, Synthesis, 2004, (15), 2545-2549
Benzene, rt, several hours
84%12 examples (5398%)
F3C OMeO
O
+
(H2C)4NCN
Me
(H2C)4NCN
CO2Me
F3C
HO
METHODS IN ORGANIC SYNTHESIS January 2005 25
Synthesis
56213 The first synthesis of 1,1-dinitrocyclopropaneE. M. Budynina, E. B. Averina, O. A. Ivanova, N. V. Yashin, T. S. Kuznetsova*, N. S. Zefirov, Synthesis, 2004, (16), 2609-2610
benzene, 5 CHC(NO2)3
CH2N2NO2NO2
+O
N
NO2
O
62% 23%
56214 The Huisgen reaction of azomethane ylide to isatins: a facile synthesis of spiro-oxindolesV. Nair*, S. Mathai, A. Augustine, S. Viji, K. V. Radhakrishnan, Synthesis, 2004, (16), 2617-2619
CH2Cl2, rt, 3 h
TFA+
82%
MeSi N
MeMe
Ph
OMe N
O
O
MeN
O
Me
NO
56215 Stereoselective reduction of -hydroxy -ketoesters: a concise synthesis of anti-,-dihydroxy estersM. Liao, W. Yao, J. Wang*, Synthesis, 2004, (16), 2633-2636
CH2Cl2, 63 C to rt, 8 h
NaBH4
11 examples, 6086%
Ph OEt
OH
O
O
Ph OEt
OH
OH
O
56216 A tandem nucleophilic addition, defluorination and destannylation. Stereospecific syntheses oftrifluoromethylated alkyl and aryl vinyl ethersY. Shen*, G. Wang, Synthesis, 2004, (16), 2637-2640
45 h, MeOH or EtOH, reflux
CH3ONa
7 examples, 7395%
SnBu3
F3-CH3C6H4
F3C H
OCH33-CH3C6H4
F3C
56217 Environmentally benign preparation of heteroaromatics from ketones or alcohols, with macroporouspolystyrenesulfonic acid and (diacetoxyiodo)benzene, followed by thioamide, amidine, and2-aminopyridineM. Weno, H. Togo*, Synthesis, 2004, (16), 2673-2677
CH3CN, reflux, 24 h
K2CO3
20 examples, 3193%
S OO
OIPh
OHN NH2 Ph
O+ +
N
OPh
56218 Reactions of 1,4-benzodiazepinic N-nitrosoamides with tosylmethyl isocyanide: a novel synthesis ofmidazolamC. del Pozo*, A. Macias, E. Alonso, J. Gonzalez*, Synthesis, 2004, (16), 2697-2703
78 C
BuLi
5 examples6882%
N
NN
Cl
NOMe
F
Me
SO2CH2CN
+ N
N
Cl
F
NTos
26 METHODS IN ORGANIC SYNTHESIS January 2005
Synthetic Communications
Synthetic Communications
56219 Infrared irradiation: effective promoter in the formation of N-benzylideneanilinesM. A. Vazquez, M. Landa, L. Reyes, R. Miranda, J. Tamariz, F. Delgado*, Synth. Commun., 2004, 34(15), 2705-2718
10 min, no solvent
26 examples (4597%) 95%
IR
Me2N
H
O NH2
Me2N
H
N
56220 A mild and efficient method for cleavage of C1N using imidazolium dichromateS. K. De*, Synth. Commun., 2004, 34(15), 2751-2755
imidazolium dichromateMeCN, reflux, 6 h
17 examples (8294%) 94%
NPh
PhOH O
Ph
Ph
56221 Highly regioselective ring opening of epoxides with polymer supported phenoxide and naphthoxide anionsB. Tamami*, N. Iranpoor, R. Rezaei, Synth. Commun., 2004, 34(15), 2789-2795
ethanol50 C, 1.5 h
28 examples (3096%) 96%
OO
O OOH
C6H4CH2N(CH3)3OC6H5CH3
Me2HC
Me2HC
56222 Titanium dioxide as a mild and efficient catalyst for conversion of epoxides to thiiranesB. Yadollahi*, S. Tangestaninejad, M. H. Habibi, Synth. Commun., 2004, 34(15), 2823-2827
TiO2, NH4SCNMeCN, reflux, 40 min
7 examples (8996%) 96%
O
OPh
S
OPh
56223 Oxidation of benzylic alcohols to carbonyl compounds with potassium permanganate in ionic liquidsA. Kumar, N. Jain, S. M. S. Chauhan*, Synth. Commun., 2004, 34(15), 2835-2842
KMnO4, [bmim][BF4]rt, 1 h
12 examples (8597%) 97%
MeO CH2OH MeO CHO
56224 Potassium fluoride assisted selective acetylation of alcohols with acetic acidJ. W. J. Bosco, B. R. Raju, A. K. Saikia*, Synth. Commun., 2004, 34(15), 2849-2855
80 C, 1.5 h
17 examples (3499%) 98%
KFOH OAcMeCO2H
56225 Selective reduction of aldehydes to alcohols using alumina with a catalytic amount of base undermicrowave irradiationP. K. Pradhan, P. Jaisankar, B. Pal, S. Dey, V. S. Giri*, Synth. Commun., 2004, 34(15), 2863-2872
Al2O3, DMAPMW 300 W (2 x 5 min), MeOH
11 examples (8095%) 95%
OHC NO2 HOH2C NO2
METHODS IN ORGANIC SYNTHESIS January 2005 27
Synthetic Communications
56226 Regioselective synthesis of chromeno[4,3-c] isoquinolin-11-ones by radical cyclizationK. C. Majumdar*, S. Sarkar, Synth. Commun., 2004, 34(16), 2873-2883
Bu3SnCl3, Na(CN)BH3AIBN, C6H6, reflux, 34 h, N2 atmosphere
O
MeN
Me3C
O
Br
O
Me3C
O8 examples6568%
56227 An eco-friendly synthesis of electrophilic alkenes catalyzed by dimethylaminopyridine under solvent-freeconditionsA. V. Narsaiah, A. K. Basak, B. Visali, K. Nagaiah*, Synth. Commun., 2004, 34(16), 2893-2901
DMAP
8085 C, 2.54 h15 examples7595%
CHO+
CN
CO2Et
CO2Et
CN
56228 Selective thioacetalization of aldehydes catalyzed by aqueous zinc tetrafluoroborateS. Islam, A. Majee*, T. Mandal, A. T. Khan, Synth. Commun., 2004, 34(16), 2911-2916
CH2Cl2, rt, 5900 min
21 examples7095%
+
CHOHS
SH HCS
SZn(BF4)
56229 Direct synthesis of N-acylalkylenediamines from carboxylic acids under mild conditionsB. P. Bandgar*, S. V. Bettigeri, Synth. Commun., 2004, 34(16), 2917-2924
triphenylphosphine, NBS2555 min, DCM
21 examples7797%
CH3(CH2)2COOH + HN NH
O
NCH3(CH2)NH
56230 A convenient preparation of enantiopure endo-2-hydroxyepicamphor and endo-3-hydroxycamphor fromcamphoric acidQ. Tan, D. Li, H. Bao, Y. Wang, J. Wen, T. You*, Synth. Commun., 2004, 34(16), 2945-2950
The starting compound is easily prepared from camphoric acid
MeOH, N2, 25 C, 12 h; or THF, HCl, 25 C
2 examples7191%
OSiMe3
OSiMe3
OH
O
H
56231 N-methylmorpholine N-oxide: a rare nonmetallic catalyst for the most efficient silylcyanation of aldehydesS. S. Kim*, G. Rajagopal, D. W. Kim, D. H. Song, Synth. Commun., 2004, 34(16), 2973-2980
1030 min, CH2Cl2
12 examples7598%
Me3SiCN, N-methylmorpholine N-oxide
H
O
CN
OSiMe3
28 METHODS IN ORGANIC SYNTHESIS January 2005
Synthetic Communications
56232 Synthesis of diacetals from aldehydes and ketones with pentaerythritol catalyzed by silica sulfate undermicrowave irrradiationT.-S. Jin*, H.-X. Wang, K.-F. Wang, T.-S. Li, Synth. Commun., 2004, 34(16), 2993-2999
benzene or toluene, 0.55.0 h
17 examples8098%
silica sulphate, hH
O O
O
O
O
56233 One-pot syntheses of amides from N-acylation of nitroarenes with esters mediated by samarium diiodideX. Wang*, H. Guo, G. Xie, Y. Zhang, Synth. Commun., 2004, 34(16), 3001-3008
THF, rt
11 examples8295%
NO2+ C
OOCH2CH3H3C
HN
CCH3
O
SmI2
56234 Synthesis of N,N-bis(2-thiazolinyl)-, N,N-bis(2-thiazolyl)-, and N,N-bis(2-pyrimidinyl)-benzenedicarboxamidesS. R. Gondi, D. Y. Son*, Synth. Commun., 2004, 34(17), 3061-3072
124 h,
EtOAcMeOHNS
NH2
+
COCl
COCl
COHN
COHN
S
N
S N 10 examples3484%
56235 Zirconium(IV) chloride catalyzed cyclization of ortho-allylphenols: synthesis of2-methyl-2,3-dihydrobenzofuransH. M. Meshram*, K. Premalatha, K. Rameshbabu, B. Eeshwaraiah, J. S. Yadav, Synth. Commun., 2004, 34(17), 3091-3097
820 h, DCM, 0 C rt, N2 atmosphere
ZrCl4
10 examples6085%OH
CH2HC
COMe
CH2
MeOC
O
56236 Efficient synthesis of 3-substituted coumarinsS. H. Mashraqui*, D. Vashi, H. D. Mistry, Synth. Commun., 2004, 34(17), 3129-3134
CH3CN, , N2, reflux, 28 h
2-chloro-1-methylpyridinium iodide(C2H5)3N
13 examples6391%
CHO
OH+
CH2CO2H
O O
56237 Silica-supported sodium hydrogen sulfate catalyzed facile transformation of p-hydroxybenzyl alcohols top-hydroxybenzyl ethers and thioethersR. Ramu, N. R. Nath, M. R. Reddy, B. Das*, Synth. Commun., 2004, 34(17), 3135-3145
1.52 h, rtNaHSO4/SiO2
21 examples8095%
+
HO
OHOH
HO
OMe
METHODS IN ORGANIC SYNTHESIS January 2005 29
Synthetic Communications
56238 Trimethylsilyl chloride: a facile and efficient reagent for one-pot synthesis of3,4-dihydropyrimidin-2(1H)-onesY. Zhu, Y. Pan*, S. Huang, Synth. Commun., 2004, 34(17), 3167-3174
rt, DMFCH3CN, 13 h
TMSCl
28 examples7697%
+OC2H5
O O
H2N NH2
O+ C6H5CHO H5C2O
NH
NH
O C6H5
O
56239 Facile and efficient deoxygenation of amine-N-oxides with gallium in waterJ. H. Han, K. I. Choi, J. H. Kim, B. W. Yoo*, Synth. Commun., 2004, 34(17), 3197-3201
0.524 h, reflux, H2O
Ga
9 examples8195%
N
CN
ON
CN
56240 A facile synthesis of 4-Ar-2-bromopyridine and its 2,2-bipyridine derivativesX.-F. Duan*, X.-H. Li, F.-Y. Li, C.-H. Huang, Synth. Commun., 2004, 34(17), 3227-3233
THF, 40 C, Pd(PPh3)4
4-CH3C6H4MgBr
3 examples4570%N
I
N
4-CH3C6H4
Br Br
56241 A novel route to 3-(O,O-diethylphosphoryl)-2,3-dihydrofurans via rhodium-catalyzed heterocycloadditionreactionD. Ging, L. Zhang, C. Yuan*, Synth. Commun., 2004, 34(18), 3251-3258
85 CH3CP
OEt
O
N2
OOEt Rh2(OAc)4Et
O+ O N
Et
H3C P(O)(OEt)2
5 examples7690%
56242 Nitration of cinnamic acids using cerium(IV) ammonium nitrate immobilized on silicaA. Messere, A. Gentili, I. Garella, F. Temussi, B. Di Blasio, A. Fiorentino*, Synth. Commun., 2004, 34(18), 3317-3324
TFA, MgSO4, rt, 20 min
CeNH4(NO2)5/SiO2
3 examples5790%
HO
COOH
HO
COOH
NO2
56243 Microwave-assisted synthesis of dihydropyrimidines in solvent-free conditionM. Mirza-Aghayan*, M. Bolourtchian, M. Hosseini, Synth. Commun., 2004, 34(18), 3335-3341
The reaction proceeds in solvent-free conditions.
2030 s, h
FeCl36H2O
8 examples3868%
O
+ Me OEt
O O
+ H2N NH2
O
NH
NEtO
O
Me O
H
30 METHODS IN ORGANIC SYNTHESIS January 2005
Synthetic Communications
56244 Nickel-catalyzed electrochemical synthesis of dihydro-benzo[b]thiophene derivativesJ. Pelletier, S. Olivero, E. Dunach*, Synth. Commun., 2004, 34(18), 3343-3348
CH3CN, electrolysis
Ni(cyclam)(BF4)25 examples5973%
Br
S S
56245 Improved synthesis of 7-(alkyl/aralkyl)guaninesA. Vidal*, I. Giraud, J.-C. Madelmont, Synth. Commun., 2004, 34(18), 3359-3365
DMA or acetic acid, HCl, 148 h, rt120 C
alkylating agent (e.g. CH3CH2I, 11 examples)
11 examples5197%
O
HO OH
HON
N N
NH
O
NH2N
N N
NH
O
NH2
CH3H2C
HCl
56246 Synthesis of iodinated naphthoquinones using morpholineiodine complexA. L. Perez*, G. Lamoureux, A. Herrera, Synth. Commun., 2004, 34(18), 3389-3397
rt, pH 2, 1060 min
K2CO3 H2O or dichloroethane
3 examples5587%
OOH
O
+O
N IH
I
OOH
OI
56247 RuCl3 catalyzed facile conversion of arylalkyl ketoximes to amidesS. K. De*, Synth. Commun., 2004, 34(18), 3431-3434
reflux, CH3CN, 1.59 h
RuCl3
11 examples4891%
NH3C
H5C6
OHC6H5NHCOCH3
56248 Synthesis of fused imidazoles based on -bromodypnoneV. Kovtunenko*, L. Potikha, A. Turov, Synth. Commun., 2004, 34(19), 3069-3613
benzene, reflux+
OPh
Ph
Br N
N NH2
N
N NH
Ph
PhO
Br
56249 A rapid and convenient synthesis of homallylic alcohols by the BarbierGrignard reactionG. J. Sormunen, D. E. Lewis*, Synth. Commun., 2004, 34(19), 3473-3480
Mg
Et2OO
C10H7+ Br
HO
H7C107 examples3482%
56250 The synthesis of 9,10-dihydro-9,10-(methaniminomethano)anthracene and N-protected derivatives viadouble reductive aminationP. Stoy, J. Rush, W. H. Pearson*, Synth. Commun., 2004, 34(19), 3481-3489
PMBNH2, NaBH3CN
78 or 6080 C, MeOH
4 examples4093%
CHO
CHO
PMP-N
METHODS IN ORGANIC SYNTHESIS January 2005 31
Synthetic Communications
56251 Novel and efficient method to synthesize N-benzyl-4-formyl-piperidineR. Sheng, Y. Hu*, Synth. Commun., 2004, 34(19), 3529-3533
MgBr2Et2O
NaOH, 2080 C3886%
H2C N O
H2C N H
O
+ (CH3)3S+IO
56252 Novel synthesis of 2-oxo-2H-benzopyrano[2,3-d]pyrimidinesH. Turki, S. Abid, Y. le Bigot, S. Fery-Forgues, R. El Gharbi*, Synth. Commun., 2004, 34(19), 3553-3563
215 h, 65 C, MeOH
6 examples2088%
+
O
NEt
Et
CN
N COEt
OEt CH2NH2
NEt
EtO
N
NNHCH2
O
56253 Efficient tetrahydropyranylation of alcohols and detetrahydropyranylation reactions in the presence ofcatalytic amount of trichloroisocyanuric acid (TCCA) as a safe, cheap industrial chemicalH. Firouzabadi*, N. Iranpoor*, H. Hazarkhani, Synth. Commun., 2004, 34(19), 3623-3630
MeOH, TCCA, rt, 38 h
dihydropyran, 6080 C, 548 hOH O
33 examples7595%
33 examples9096%
TCCA: trichloroisocyanuric acid
N N
NCl
O
ClO
Cl
O
56254 -PCC and -PCC-SiO2 as efficient reagents for oxidation of thiols to disulfidesM. M. Khodaei*, P. Salehi, M. Goodarzi, A. Yazdanipour, Synth. Commun., 2004, 34(20), 3661-3666
-PCC-SiO2CH2Cl2, rt, 4 h
12 substrate examples (3895%) 95%
CH2SH
56255 Potassium dodecatungstocobaltate trihydrate (K5CoW12O403H2O) as an efficient catalyst for aminolysisof epoxidesE. Rafiee*, S. Tangestaninejad, M. H. Habibi, V. Mirkhani, Synth. Commun., 2004, 34(20), 3673-3681
MeCN, reflux, 5.5 h90 examples (4599%) 99%
K5CoW12O403H2OOCl H2N Br
OH
CH2ClNHBr
56256 Efficient and selective formation of mixed acetals by Nafion-H SAC-13 silica nanocomposite solid acidcatalystI. Ledneczki, A. Molnar*, Synth. Commun., 2004, 34(20), 3683-3690
reflux, 5 min32 examples (up to 100%) 100%
SAC-13OH (BuO)2CH2 O
CH2OBu
56257 Stereoselective synthesis of cis-1-aryl-2-benzoyl-3,3-dicyanocyclopropanes in the presence of KF2H2OZ. Ren*, W. Cao, W. Ding, Y. Wang, L. Wang, Synth. Commun., 2004, 34(20), 3785-3792
DME, rt, 4 h
11 examples (8695%) 95%
KF2H2OC6H5CH C(CN)2CN
CNC6H5
COPh
Ph3AsCH2COPhBr
32 METHODS IN ORGANIC SYNTHESIS January 2005
Tetrahedron
56258 Microwave-induced rapid access to aromatic and heteroaromatic sulfonamides under solvent-freeconditions without using external baseA. K. Sharma, S. K. Das*, Synth. Commun., 2004, 34(20), 3807-3819
6 min
28 examples (3094%) 94%
MW
NH2
Br Br
HN
SMeSO2Cl
Ph
O O
56259 Bismuth subnitrate catalyzed efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones: an improvedprotocol for the Biginelli reactionY. T. Reddy, B. Rajitha*, P. N. Reddy, B. S. Kumar, V. P. Rao, Synth. Commun., 2004, 34(20), 3821-3825
MeCN, 7080 C, 1.5 h
17 examples (8896%) 96%
BiONO3O O
Ph H NH2 NH3 Me OMe
O O
NH
N
Ph
O
O
MeO
Tetrahedron
56260 Calcium phosphate-vanadate apatite (CPVAP)-catalyzed aerobic oxidation of propaygylic alcohols withmolecular oxygenY. Maeda, Y. Washitake, T. Nishimura*, K. Iwai, T. Yamauchi, S. Uemura*, Tetrahedron, 2004, 60(41), 9031-9036
n-PrCN, 100 C, 20 h, O2 (1 atm)
99%18 substrates (2099%)
Calcium phosphate vanadate apatite
Me
OH
Me
O
56261 Enantioselective oxidative coupling of methyl 3-hydroxy-2-naphthoate using mono-N-alkylatedoctahydrobinaphthyl-2,2-diamine ligandK. H. Kim, D.-W. Lee, Y.-S. Lee, D.-H. Ko, D.-C. Ha*, Tetrahedron, 2004, 60(41), 9037-9042
CH2Cl2
98%, 42% ee15 examples (5699%)
CuCl, O2, mol sieves, [N]CO2Me
OH
CO2Me
OH
CO2Me
OH
NH2NH2
[N] =
56262 Scope and limitation of montmorillonite K 10 catalysed opening of epoxide rings by amineA. K. Chakraborti*, A. Kondaskar, S. Rudrawar, Tetrahedron, 2004, 60(41), 9085-9091
rt, 3 h
98%16 substrates (69100%)
Montmorillonite K 10O
NH2
+
HO HN
METHODS IN ORGANIC SYNTHESIS January 2005 33
Tetrahedron
56263 -Hydroxy carboxylic acids as ligands for enantioselective diethylzinc additions to aromatic and aliphaticaldehydesT. Bauer*, J. Gajewiak, Tetrahedron, 2004, 60(41), 9163-9170
Et2Zn, 28 C, 19 h97%, 77% ee18 substrates (7097%, 5283% ee)
H3CO CHO H3COOH
OH
O
HO
Ph
56264 Enantioselective total synthesis of ()-strychnine: development of a highly practical catalytic asymmetriccarboncarbon bond formation and domino cyclizationT. Ohshima, Y. Xu, R. Takita, M. Shibasaki*, Tetrahedron, 2004, 60(43), 9569-9588
KO-t-Bu THF, rt, 4 mol sieve
95%, >99% ee9 examples (7496%, 93>99% ee)
[Al]+
CO2Me
O CO2MeO
CO2Me
CO2MeH
OO
AlOO
Li[Al] =
56265 Sequential ring-closing metathesis/Pd-catalyzed, Si-assisted cross-coupling reactoins: general synthesisof highly substituted unsaturated alcohols and medium-sized rings containing a 1,3-cis-cis diene unitS. E. Denmark*, S.-M. Yang, Tetrahedron, 2004, 60(43), 9695-9708
rt, 30 min
92%11 examples (9193%)
TBAF, Pd(dba)2Si
O
Me Me OH
I
OMe+
56266 Combinatorial approach to the asymmetric hydrogenation of -acylamino acrylates: use of mixtures ofchiral monodentate P-ligandsM. T. Reetz*, X. Li, Tetrahedron, 2004, 60(43), 9709-9714
CH2Cl2
92%171 examples (8.3100%, 13.498.8% ee)
L2Rh(COD)BF4R'
HNO
CO2R''
R' = CH3, C2H5, n-C3H7, C6H5R'' = CH3, C2H5
R'
HNO
CO2R''
L = chiral monodentate P ligands
56267 Palladium-catalyzed -arylation of N-protected 2-piperidinonesA. de Filippis, D. G. Pardo, J. Cossy*, Tetrahedron, 2004, 60(43), 9757-9767
THF, 65 C
97%38 examples (099%)
Pd(dba)2, [L][L] =N
BnO Br
NBn
O
+NH2
Cy2P
56268 Highly diastereo- and enantioselective reactions of enecarbamates with an aldehydeR. Matsubara, P. Vital, Y. Nakamura, H. Kiyohara, S. Kobayashi*, Tetrahedron, 2004, 60(43), 9769-9784
CH2Cl2
95%, 98% ee17 examples (8297%, 9498% ee)
CuClO44CH3CN, [L][L] =
+
O
EtOO
H HN
Ph
O
OBnMe
O
EtOOH
Me
N
Ph
O
OBnN N
p-Br-C6H4 p-Br-C6H4
34 METHODS IN ORGANIC SYNTHESIS January 2005
Tetrahedron Letters
Tetrahedron Letters
56269 Palladium-catalysed three component synthesis of ,-unsaturated amidines and imidatesK. Kishore, R. Tetela, R. J. Whitby*, M. E. Light, M. B. Hurtshouse, Tetrahedron Lett., 2004, 45(38), 6991-6994
tBuNCPdCl2, dppf, Cs2CO3, 65 C, toluene, 1530 min
PhBr NH
Ph N
NtBu
56270 Palladium catalysed synthesis of cyclic amidines and imidatesC. G. Saluste, S. Crumpler, M. Furber, R. J. Whitby*, Tetrahedron Lett., 2004, 45(38), 6995-6996
PdCl2, dppftoluene, 220 h, 109 C, Cs2CO3 or NaOtBu
3884%12 examples
Br
NH2tBuNC N
HN tBu
56271 Preparation of the conjugated polyene chains with the 1,4-dimethyl substitutionH.-S. Jeon, S. Koo*, Tetrahedron Lett., 2004, 45(38), 7023-7026
n-BuLi, DBUTHF, benzene
5292%4 examples
Cl CO2Et
CO2Et SO2Ph CO2Et
CO2Et
56272 Nitroalkanes and ethyl glyoxalate as common precursors for the preparation of both -keto esters and,-unsaturated estersR. Ballini*, D. Fiorini, A. Palmieri, Tetrahedron Lett., 2004, 45(38), 7027-7029
MeSO2Cl, Amberlyst A-21Et3N, CH2Cl2, rt then 0 C, 1.5 h
6594%12 examples
H3CH2C NO2
O
OEtO
H3CH2C
NO2COOEt
56273 -Addition of activated methylenes to alyknoates. A straightforward synthesis of multifunctionalcompoundsM. Hanedanian, O. Loreau, F. Taran*, C. Mioskowski*, Tetrahedron Lett., 2004, 45(38), 7035-7038
PPh3AcOHAcONatoluene, 80110 C, up to 4h
2388%11 examples
COOEt
O O
COOEt
OOH
56274 Regioselective Pd-catalyzed alkylative lactonizations of 4-hydroxy-2-alkynecarboxylates withorganoboronic acidsC. H. Oh*, S. J. Park, J. H. Ryu, A. K. Gupta, Tetrahedron Lett., 2004, 45(38), 7039-7042
AcOH, 1,4-dioxane, 80 C
yield: 70%ee: 95%
EtOOCEtOOC
O
PhB(OH)2EtOOCEtOOC
O
Pd(PPh3)4
METHODS IN ORGANIC SYNTHESIS January 2005 35
Tetrahedron Letters
56275 A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on thestereoselectivityK. Sasaki, S. Matsumura, K. Toshima*, Tetrahedron Lett., 2004, 45(38), 7043-7047
protic acid, ionic liquid25 C, 14 h
8289%6 examples
OBnO
BnO BnO F
BnO
HOOBnO
BnO BnO O
BnO
56276 A convenient synthesis of 3-amino-4-imino(thioxo)-imidazolidin-2-onesT. Kurz*, K. Widyan, Tetrahedron Lett., 2004, 45(38), 7049-7051
CDI or CDT & Et3N or THF, NaH, H2NNHC6H5
5773%10 examples
EtO PO
EtONH
CN EtO PO
EtOHN
N
NH
NH
OC6H5
56277 A two-step synthesis of aminopropylpiperidines via aminopropargylpyridines, suitable for the synthesisof a new class of 5-HT4 ligandsO. Russo, M. Alami*, J.-D. Brion, S. Sicsic, I. Berque-Bestel*, Tetrahedron Lett., 2004, 45(38), 7069-7072
Et3N, DMF, 80 C, PdCl2(PPh3)2CuI
5393%6 examples
KN(Boc)2
N Br Br+
NNBoc2
56278 The simple solvent-free synthesis of 1H-quinazoline-2,4-diones using supercritical carbon dioxide andcatalytic amount of baseT. Mizuno*, T. Wai, Y. Ishino, Tetrahedron Lett., 2004, 45(38), 7073-7075
scCO2, 10 MPa, 80 C, 4 h
4 examples5497%
baseNH2
CNNH
HN
O
O
56279 Highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to indolenatural product synthesisS. M. Allin*, C. I. Thomas, J. E. Allard, K. Doyle, M. R. J. Elsegood, Tetrahedron Lett., 2004, 45(38), 7103-7105
rt, 20 h
yield: 95%de 100%
HCl, EtOH
N
O
NHO
H
NH
NH
O
HOH
36 METHODS IN ORGANIC SYNTHESIS January 2005
Tetrahedron Letters
56280 General facile synthesis of 2,5-diarylheteropentalenesP. Vachal*, L. M. Toth, Tetrahedron Lett., 2004, 45(38), 7157-7161
Na2Co3, H2O, DMF, 2585 C, 23 h
9 examples7491%
PhI, Pd(Ph3P)4HS(HO)2B
S
Ph
56281 Iodine-catalyzed synthesis of -keto enol estersR. S. Bhosale, S. V. Bhosale, S. V. Bhosale, T. Wang, P. K. Zubaidha*, Tetrahedron Lett., 2004, 45(39), 7187-7188
I2, alcoholrt, 37 min
O
O
O
OMe
9396%9 examples
56282 Synthesis of -hydroxy nitriles and 1,3-amino alcohols from epoxides using acetone cyanohydrin as aLiCN precursorJ. A. Ciaccio*, M. Smrtka, W. A. Miao, D. Rucando, Tetrahedron Lett., 2004, 45(39), 7201-7204
LiCNacetone0.253 h, THF
6590%12 examples
O OH
(CH2)10CH3NC OH
(CH2)10CH3
HO
56283 Catalysis of highly stereoselective Mannich-type reactions of ketones with -imino esters by apyrrolidine-sulfonamide. Synthesis of unnatural -amino acidsW. Wang*, J. Wang, H. Li, Tetrahedron Lett., 2004, 45(39), 7243-7246
rt, DMSO, 220 h
yield: 7491%ee: 9699%8 examples
NH HN S
O
OCF3
O+
N
HEtO2C
PMP
CO2Et
O NHPMP
56284 Enantioselective syntheses of bicyclo[3.1.0]hexane carboxylic acid derivatives by intramolecularcyclopropanationN. Yoshikawa*, L. Tan, N. Yasuda, R. P. Volante, R. D. Tillyer, Tetrahedron Lett., 2004, 45(39), 7261-7264
3857%2 examples
1. pyrrolidine, reflux2. TBSCl. imidazole, DMF, rt3. NMO, OsO4, acetoneH2O, rt4. SOCl2, Et3N, toluene, 0 C5. LiHMDS, THF, 78 C
O
H
H
HHHO
HOTBS
O
N
METHODS IN ORGANIC SYNTHESIS January 2005 37
Tetrahedron Letters
56285 An efficient and green protocol for the preparation of cycloalkanols: a practical synthesis of venlafaxineS. P. Chavan*, D. A. Khobragade, S. K. Kamat, L. Sivadasan, K. Balakrishnan, T. Ravindranathan, M. K. Gurjar, U. R. Kalkote,Tetrahedron Lett., 2004, 45(39), 7291-7295
5697%12 examples
H2O, 45120 min, phase transfer catalysis
NaOH or KOH
OMe
CN
O
+
OMe
CNOH
56286 Synthesis of 1,2-dihydroisoquinolines via the reaction of ortho-alkynylarylamines with bis--allylpalladiumM. Ohtaka, H. Nakamura, Y. Yamamoto*, Tetrahedron Lett., 2004, 45(39), 7339-7341
Cu(OAc)2, CH3CN, 50 C
+
NBn
PhSnBu3
Cl+
PdCl
PdCl
N
Ph
Bn
56287 A novel procedure for the synthesis of multifunctional ketones through the Fukuyama coupling reactionemploying dialkylzincsY. Mori, M. Seki*, Tetrahedron Lett., 2004, 45(39), 7343-7345
ZnBr, THF, toluene, DMF, 20 C, 1748 h
Et2Zn, Pd/C
MeO
O
SEt
O
O
Et
5695%6 examples
56288 Highly regioselective ring opening of epoxides using NaN3: a short and efficient synthesis of()-cytoxazoneJ. Boruwa, J. C. Borah, B. Kalita, N. C. Barua*, Tetrahedron Lett., 2004, 45(39), 7355-7358
CH3CN, 1.01.6 h
NaN3, 4 molecular sieves
9097%9 examples
O
Cl N3 Cl
OH
56289 Bismuth trichloride catalyzed synthesis of -aminonitrilesS. K. De*, R. A. Gibbs, Tetrahedron Lett., 2004, 45(40), 7407-7408
BiCl3, TMSCNCH3CN, rt, 510 h
CHO + NH2 HN
CN
38 METHODS IN ORGANIC SYNTHESIS January 2005
Tetrahedron Letters
56290 Synthesis of 4b,5,10a,11-tetrahydroindeno[1,2-b]-quinolin-10-ones from BaylisHillman adductsC. G. Lee, Y. Lee, S. GowriSankar, J. N. Kim*, Tetrahedron Lett., 2004, 45(40), 7409-7413
PPA120170 C, 0.518 h
NH HN
O
+
N7 examples5062%
5 examples422%
56291 A simple, efficient, and highly selective method for the iodination of alcohols using ZrCl4/NaIH. Firouzabadi*, N. Iranpoor*, M. Jafarpour, Tetrahedron Lett., 2004, 45(40), 7451-7454
ZrCl4/NaI2120 min, CH3CN
14 examples7597%
OH I
56292 Curtius rearrangement and Wolff homologation of functionalized peroxidesP. H. Dussault*, C. Xu, Tetrahedron Lett., 2004, 45(40), 7455-7457
EtOC(O)Cl then CH2N2
11 examples4799%
O OH
t-BuO O
O CHN2
t-BuO O
56293 Quinone methide initiated cyclization reaction: synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolinesB. C. Raju*, P. Neelakantan, U. T. Bhalerao*, Tetrahedron Lett., 2004, 45(40), 7487-7489
3 examples7886%
MeO
MeONHTS
+
H3COBn
CH3
CH2Br
H3COH
CH3
NTsHN
OMe
OMe
1. NaH/DMF2. Pd/C, H23. Ag2O, DCM4. ZnCl2, DCM
56294 Opening of epoxides with aromatic amines promoted by indium tribromide: a mild and efficient methodfor the synthesis of -amino alcoholsJ. R. Rodriguez, A. Navarro*, Tetrahedron Lett., 2004, 45(40), 7495-7498
16 examples6596%
+InBr3
CH2Cl2, rtO
7tBu NH2 7
OHNH
tBu
56295 Synthesis and reactivity of enantiomerically pure N-alkyl-2-alkenyl azetidinium saltsF. Couty*, F. Durrat, G. Evano, D. Prim, Tetrahedron Lett., 2004, 45(40), 7525-7528
7 examples6994%up to 72%
KHMDS or PhLi
N
Ph
Bn MeMe
N
Ph
Me
PhTfO
Bn
METHODS IN ORGANIC SYNTHESIS January 2005 39
Books, Reviews and Conference Proceedings
Books, Reviews and Conference Proceedings
56296 DNA-Templated organic synthesis: Natures strategy for controlling chemical reactivity applied tosynthetic moleculesX. Li, D. R. Liu*, Angew. Chem., Int. Ed., 2004, 43(37), 4848-4870
A review, with 172 references, describing some representative early examples of nucleic acid templated synthesis,an analysis of current understanding of this technique, emerging applications and future challenges.
56297 N-Heterocyclic carbenes: reagents, not just ligands!V. Nair*, S. Bindu, V. Sreekumar, Angew. Chem., Int. Ed., 2004, 43(39), 5130-5135
A review, with 37 references, covering the use of N-heterocyclic carbenes as catalyst and nucleophilic reagents intransesterification, nucleophilic aromatic substitution, cycloaddition and asymmetric reactions.
56298 In the golden age of organocatalysisP. I. Dalko*, L. Moisan, Angew. Chem., Int. Ed., 2004, 43(39), 5138-5175
A review, with 251 references, covering the use of organic compounds as catalysts in a diverse range of reactions.
56299 Stereoselective synthesis using diastereotopic groupsR. W. Hoffmann*, Synthesis, 2004, (13), 2075-2090
A review, with 104 references, of stereoselective synthesis using diastereotopic group differentiating reactions,with conformationally flexible molecules.
56300 Palladium catalysts for the Suzuki cross-coupling reaction: an overview of recent advancesF. Bellina, A. Carpita, R. Rossi*, Synthesis, 2004, (15), 2419-2440
A review, with 206 references, of work until March 2004 on new catalyst systems for palladium catalysed Suzukicross-coupling rections of organic electrophiles and organoboron compounds.
56301 Intermolecular CH insertions of donor/acceptor-substituted rhodium carbenoids: a practical solution forcatalytic enantioselective CH activationH. M. L. Davies*, O. Loe, Synthesis, 2004, (16), 2595-2608
A review, with 58 references, covering recent developments in the rhodium-catalyzed intermolecular CHinsertion chemistry of diazo compounds.
56302 Current methods for the synthesis of 2-substituted azolesC. A. Zificsak, D. J. Hlasta*, Tetrahedron, 2004, 60(41), 8991-9016
A review, with 256 references, of recent literature focusing on new methods of substitution to construct CC bondsin preparing azole derivatives.
56303 The Reformatsky reaction in organic synthesis. Recent advancesR. Ocampo, W. R. Dolbier, Jr.*, Tetrahedron, 2004, 60(42), 9325-9374
A review, with 369 references, of the recent progress in the uses of Reformatsky reactions in synthetic organicchemistry. Included are recent work in diastereo- and enantioselective reactions.
40 METHODS IN ORGANIC SYNTHESIS January 2005
Author Index
Author Index
Abe, H. 56191Abid, S. 56252Aikawa, K. 56186Alami, M. 56277Albert, M. 56151Albu, S. 56096Alcazar, E. 56199Alesi, S. 56107Alexakis, A. 56174Allard, J. E. 56279Allin, S. M. 56279Alonso, E. 56218Alper, H. 56171Alves, E. F. 56110Anderson, K. 56128Andersson, P. 56196Aubert, C. 56127Augustine, A. 56214Averina, E. B. 56213Azizian, J. 56203Bacque, E. 56182Balakrishnan, K. 56285Ballini, R. 56124, 56272Bandgar, B. P. 56229Banerjee, J. 56161Bao, H. 56230Barboni, L. 56124Barrett, A. G. M. 56163Barua, N. C. 56288Basak, A. K. 56227Bauer, T. 56263Beller, M. 56083, 56086Bellina, F. 56300Bennacer, B. 56179Bergmann, R. G. 56089,
56090Berque-Bestel, I. 56277Bettigeri, S. V. 56229Bhalerao, U. T. 56293Bhor, S. 56086Bhosale, R. S. 56281Bhosale, S. V. 56281, 56281Biermann, U. 56134Bindu, S. 56297Blaszczyk, A. 56153Boas, U. 56207Bolm, C. 56157Bolourtchian, M. 56243Borah, J. C. 56288Boruwa, J. 56288Bosco, J. W. J. 56224Boto, A. 56194BouzBouz, S. 56169Bovin, Y. 56156Bowser, A. M. 56166Braga, A. L. 56110Brion, J.-D. 56277Bryliakov, K. P. 56085Buchwald, S. 56128Budynina, E. M. 56213Cadran, N. 56127Campbell, J. E. 56143Cao, W. 56257Cariou, K. 56127Carlo, G. 56124
Carpita, A. 56300Carreira, E. 56198Carreno, M. 56175Castedo, L. 56133Chakraborti, A. K. 56262Chan, A. S. C. 56104Chan, K. S. 56104Chandraiah, L. 56208Chandrasekhar, S. 56108Chapman, C. 56196Chatani, N. 56180Chauhan, S. M. S. 56223Chavan, S. P. 56285Chavarot, M. 56103Che, C.-M. 56082Chen, F.-X. 56204Chen, J. 56082Chen, W. 56159Cho, G. Y. 56157Choi, K. I. 56239Choudary, B. 56126Christensen, J. B. 56207Ciaccio, J. A. 56282Ciufolini, M. A. 56156Colacot, T. 56189Colobert, F. 56175Corey, E. J. 56164, 56165Cossy, J. 56169, 56267Couty, F. 56295Cozzi, P. G. 56107Crumpler, S. 56270Cui, J. 56105Dalko, P. I. 56298Das, B. 56161, 56200,
56237Das, S. K. 56258Davies, H. M. L. 56142,
56301De, S. K. 56220, 56247,
56289de Filippis, A. 56267Defieber, C. 56198del Pozo, C. 56218Delgado, A. 56133Delgado, F. 56219Deng, J. G. 56100Denmark, S. E. 56265Deprele, S. 56195Dey, S. 56225Di Blasio, B. 56242Diesen, J. 56196Ding, K. 56135Ding, W. 56257Dingerdissen, U. 56083Dobler, C. 56086Dolbier, W. R., Jr. 56303Dommisse, R. A. 56109Dong, C. 56171Dong, Y. 56211Doyle, K. 56279Duan, X.-F. 56240Dunach, E. 56244Durrat, F. 56295Dussault, P. H. 56292Early, T. R. 56098
Ebitani, K. 56139Eeshwaraiah, B. 56235Ekstrand, M. 56106Ekthawatchai, S. 56172El Gharbi, R. 56252El Qacemi, M. 56182Elbing, M. 56153Elsegood, M. R. J. 56279Enthaler, S. 56083Evano, G. 56295Fabbri, D. 56188Feng, X. 56204Fensterbank, L. 56127Fernandez, S. 56192Ferrero, M. 56192Fery-Forgues, S. 56252Fiorentino, A. 56242Fiorini, D. 56272Firouzabadi, H. 56253,
56291Fort, Y. 56209Frolich, R. 56183Fujii, T. 56173Fujioka, S. 56148Fujita, K. 56173Fujita, K.-i. 56092Fujiwara, M. 56179Funabiki, K. 56093Furber, M. 56270Gajare, A. S. 56119Gajewiak, J. 56263Garcia, J. 56192Garella, I. 56242Gentili, A. 56242Ghosh, R. 56152Gibbs, R. A. 56289Ging, D. 56241Giralt, E. 56121Giraud, I. 56245Giri, V. S. 56225Godet, T. 56156Gommermann, N. 56102Gondi, S. R. 56234Gonzalez, J. 56218Goodarzi, M. 56254Gotor, V. 56192Goushi, S. 56093GowriSankar, S. 56290Guo, H. 56233Gupta, A. 56168Gupta, A. K. 56274Gupta, M. K. 56101Gurjar, M. K. 56285Guy, I. L. 56097Ha, D.-C. 56261Habibi, M. H. 56222, 56255Hagemann, B. 56083Hallur, M. 56168Hampel, N. 56091Han, J. H. 56239Han, W. 56158Hancock, F. E. 56159Hanedanian, M. 56273Hara, T. 56139Harms, K. 56170
Harrowven, D. C. 56097Hashimoto, S. 56193Haufe, G. 56183Hayashi, T. 56167Hazarkhani, H. 56253Hazell, R. G. 56096Hernandez, D. 56194Hernandez, R. 56194Herrera, A. 56246Herve, G. 56127Hirao, T. 56210Hlasta, D. J. 56302Hoffmann, M. 56091Hoffmann, R. W. 56299Hoge, G. 56181Holmes, A. B. 56098Hong, B. 56168Hosseini, M. 56243Hoveyda, A. 56140Hoveyda, A. H. 56143Hu, J. 56084, 56114Hu, X. 56178Hu, Y. 56251Hua, Z. 56155Huang, C.-H. 56240Huang, S. 56238Hugl, H. 56086Hurtshouse, M. B. 56269Ichikawa, E. 56151Ikagawa, A. 56145Ikariya, T. 56145Imagawa, H. 56184Iranpoor, N. 56221, 56253,
56291Ishino, Y. 56278Ishizuka, T. 56193Islam, S. 56228Itami, K. 56185Ivanova, O. A. 56213Iwai, K. 56260Jafarpour, M. 56291Jagadeesh, B. 56101Jain, N. 56223Jaisankar, P. 56225Jansson, J. 56157Jantos, K. 56170Jasoni, R. L. 56114Jeon, H.-S. 56271Jiao, N. 56115Jin, Q. 56142Jin, T. 56112Jin, T.-S. 56232Jin, Z. 56155Johannesen, S. A. 56096Johnson, J. S. 56120Junge, K. 56083Kacprzynski, M. 56140Kakiuchi, F. 56180Kalita, B. 56288Kalkote, U. R. 56285Kamat, S. K. 56285Kambe, N. 56160Kamijo, S. 56112Kamounah, F. S. 56207Kanai, M. 56151
METHODS IN ORGANIC SYNTHESIS January
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