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Asymmetric Synthesis

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Edited by Mathias Christmann and Stefan Brase

Asymmetric Synthesis

More Methods and Applications

The Editors

Prof. Dr. Mathias ChristmannTechnische UniversitatOrganische ChemieOtto-Hahn-Str. 644227 DortmundGermany

Prof. Dr. Stefan BraseInstitut fur Technologie (KIT)Inst. f. Organische ChemieFritz-Haber-Weg 676131 KarlsruheGermany

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V

Contents

List of Contributors XVII

1 Catalytic Enantioselective Alkylation of Prochiral Ketone Enolates 1Corey M. Reeves and Brian M. StoltzBackground 1Strategy and Results 1Asymmetric Allylic Alkylation in Total Synthesis 4Conclusions 8CV of Corey M. Reeves 8CV of Brian M. Stoltz 8References 8

2 Point-to-Planar Chirality Transfer in Total Synthesis: Scalable andProgrammable Synthesis of Haouamine A and Its Atropisomer 11Noah Z. Burns and Phil S. BaranIntroduction 11Synthetic Strategy Featuring Point-to-Planar Chirality Transfer 11Programmable Synthesis of Haouamine A and Its Atropisomer 12CV of Noah Z. Burns 15CV of Phil S. Baran 15References 16

3 Tethered Aminohydroxylation 17Timothy J. Donohoe and Stefanie MeschIntroduction and Background 17Tethered Aminohydroxylation 17

a) First Generation of Reoxidants 18b) N-Sulfonyloxy Carbamates 19c) Carbonyloxycarbamates as Reoxidants for Osmium 21

Amide-Based Reoxidants 22Evidence for the Mechanism of the TA Reaction 23Applications in Organic Synthesis 24Conclusion and Future Work 24

VI Contents

CV of Timothy J. Donohoe 24CV of Stefanie Mesch 26References 26

4 Organocatalyzed Transformations of α, β-Unsaturated CarbonylCompounds through Iminium Ion Intermediates 29Julian H. Rowley and Nicholas C. O. TomkinsonCV of Nicholas C. O. Tomkinson 33CV of Julian H. Rowley 33References 34

5 The Renaissance of Silicon-Stereogenic Silanes: A Personal Account 35Andreas Weickgenannt and Martin OestreichBackground 35Results 36

a) Intermolecular Chirality Transfer from Silicon to Carbon:Diastereoselective Palladium(II)-Catalyzed C–Si BondFormation 36

b) Silicon-Stereogenic Silane as Stereochemical Probe:B(C6F5)3-Catalyzed Carbonyl Reduction 37

c) Kinetic Resolution with Silicon-Stereogenic Silanes:Cu–H-Catalyzed Diastereoselective Si–O Coupling 39

Conclusion 41CV of Martin Oestreich 41CV of Andreas Weickgenannt 41References 41

6 Asymmetric Dienamine Activation 43Mathias ChristmannIntroduction 43Historic Background 43Results 44Conclusion 47CV of Mathias Christmann 47References 47

7 Asymmetric Brønsted Acid Catalysis 49Iuliana Atodiresei, Uxue Uria, and Magnus RuepingIntroduction and Background 49Strategy 49Results 50Summary 52CV of Iuliana Atodiresei 52CV of Uxue Uria 52

Contents VII

CV of Magnus Rueping 53References 53

8 Quaternary Stereogenic Centers by Enantioselective β-CarbonEliminations from tert-Cyclobutanols 55Nicolai Cramer and Tobias SeiserBackground 55Objective: Enantioselective Formation of Quaternary StereogenicCenters in Combination with Reactive Alkyl-RhodiumIntermediates 56Selective Generation of the Alkyl-Rhodium Species and Its DownstreamReactivities 56CV of Nicolai Cramer 57CV of Tobias Seiser 59References 59

9 Total Synthesis of Oseltamivir and ABT-341 Using One-PotTechnology 61Hayato Ishikawa and Yujiro HayashiIntroduction 61Results 61

a) Total Synthesis of (−)-Oseltamivir via Two One-Pot Processes 61b) Total Synthesis of ABT-341 by One-Pot Sequence 63

Conclusions 64CV of Yujiro Hayashi 65CV of Hayato Ishikawa 65References 65

10 Enantioselective Annulations with Chiral N-Mesityl N-HeterocyclicCarbenes 67Jessada Mahatthananchai and Jeffrey W. BodeIntroduction 67Catalytic Generation of Chiral Enolate Equivalents 68Catalytic Generation of Homoenolate Equivalents 70Enantioselective Cascade Reactions Catalyzed by Chiral N-HeterocyclicCarbenes 70Catalytic Annulations via α, β-Unsaturated Acyl Azoliums 72Conclusions 74CV of Jeffrey Bode 76CV of Jessada Mahatthananchai 76References 76

11 Asymmetric Counteranion-Directed Catalysis (ACDC) 79Manuel Mahlau and Benjamin ListConcept 79

VIII Contents

Application of ACDC to Organocatalysis 80Application of ACDC to Transition Metal Catalysis 81Application of ACDC to Lewis Acid Catalysis 82CV of Manuel Mahlau 83CV of Prof. Dr. Benjamin List 84References 84

12 Enantioselective Organo-SOMO Catalysis: a Novel Activation Modefor Asymmetric Synthesis 87David W. C. MacMillan and Sebastian RendlerBackground 87Objective 88Results 90CV of David W.C. MacMillan 92CV of Sebastian Rendler 93References 93

13 Enantioselective Passerini Reaction 95Qian Wang, Jieping Zhu, and Mei-Xiang WangIntroduction 95Background 95Results 96Conclusion and Perspective 99CV of Qian Wang 99CV of Jieping Zhu 99CV of Mei-Xiang Wang 100References 100

14 Rapid Enantiomeric Excess Determination 103Oliver TrappCV of Oliver Trapp 106References 106

15 Asymmetric Catalysis of Reversible Reactions 109Lukas HintermannThermochemistry of Asymmetric Catalyses Close to theEquilibrium 109Kinetic Modeling of a Reversible Asymmetric CatalyticReaction 111Case Study: a Reversible Asymmetric OrganocatalyticReaction 112Conclusions 115CV of Lukas Hintermann 115References 115

Contents IX

16 Exploiting Fluorine Conformational Effects in Organocatalyst Design: TheFluorine–Iminium Ion Gauche Effect 117Christof Sparr, Lucie E. Zimmer, and Ryan GilmourCV of C. Sparr 121CV of L. Zimmer 123CV of R. Gilmour 123References 124

17 Dutch Resolution 125Richard M. KelloggCV of Richard M. Kellogg 129References 129

18 Construction of anti-Me-OH Vicinal Relationships in Polyketides 131Vaidotas Navickas and Martin E. MaierIntroduction 131Marshall–Tamaru Reaction 131Conclusions 136CV of Vaidotas Navickas 136CV of Martin E. Maier 136References 136

19 Photoswitchable General Base Catalysts 139Philipp Viehmann and Stefan HechtIntroduction and Background 139Strategy and Results 141Outlook 143CV of Philipp Viehmann 144CV of Stefan Hecht 145References 145

20 Asymmetric Halonium Addition to Olefins 147Scott A. Snyder and Alexandria P. BrucksIntroduction 147Intramolecular Lactonizations, Etherifications, and Aminations 147Polyene Cyclizations 150Intermolecular Additions to Alkenes 150Conclusion 152CV of Scott A. Snyder 154CV of Alexandria P. Brucks 154References 154

21 Catalytic Asymmetric Gosteli–Claisen Rearrangement (CAGC) 157Julia Rehbein and Martin HiersemannCV of Julia Rehbein 162

X Contents

CV of Martin Hiersemann 162

References 162

22 Biomimetic Total Synthesis of the Penifulvin Family 165Tanja Gaich and Johann Mulzer

Introduction 165

The Penifulvin Family: Isolation and Biogenetic Origin 166

Total Syntheses of Penifulvins A, B, and C 168

Summary 175

CV of Prof. Johann Mulzer 175

CV of Tanja Gaich 175

References 176

23 Catalyst-Controlled 1,3-Polyol Syntheses 179Tobias Harschneck and Stefan F. Kirsch

CV of Stefan F. Kirsch 184

CV of Tobias Harschneck 184

References 185

24 Enantioselective Carbonyl Allylation and Crotylation from the AlcoholOxidation Level via C–C Bond Forming Transfer Hydrogenation 187Joseph Moran and Michael J. Krische

Introduction and Background 187

Strategy 187

Results 188

CV of Michael Krische 190

CV of Joseph Moran 191

References 195

25 Stereoselective Synthesis with Hypervalent Iodine Reagents 197Umar Farid and Thomas Wirth

CV of Umar Farid 201

CV of Thomas Wirth 201

References 202

26 Asymmetric Gold-Catalyzed Reactions 205Nuria Huguet and Antonio M. Echavarren

Introduction 205

Diphosphine-Gold Complexes in Enantioselective Catalysis 205

Monophosphine-Gold Complexes in Enantioselective Catalysis 208

CV of Nuria Huguet 209

CV of Antonio M. Echavarren 210

References 210

Contents XI

27 Asymmetric Catalysis in the Total Synthesis of Lipids andPolyketides 213Santiago Barroso and Adriaan J. MinnaardBackground 213Tuberculostearic Acid: One Isolated Methyl Group 213Ant Pheromones: Vicinal Methyl Branches 214Deoxypropionates: 1,3-Methyl Arrays 215Membrane-Spanning Lipids: 1,4-Dimethyl Units 215Saturated Isoprenoids: 1,5-Methyl Arrays 217CV of Santiago Barroso 218CV of Adriaan J. Minnaard 218References 218

28 The Evolving Role of Biocatalysis in Asymmetric Synthesis 221Melanie Hall, Wolfgang Kroutil, and Kurt FaberBackground – First- and Second-Generation Biotransformations 221Results–Third-Generation Biotransformations 221

a) Asymmetric Bioreduction of C=C Bonds 221b) Asymmetric Transamination 226

Conclusions and Future Perspectives 228CV of Melanie Hall 229CV of Wolfgang Kroutil 229CV of Kurt Faber 229References 229

29 Bifunctional Thiourea Catalysts 233Yoshiji Takemoto and Tsubasa InokumaBackground 233Results 233

a) Aminothiourea 233b) Hydroxythiourea 235

CV of Yoshiji Takemoto 236CV of Tsubasa Inokuma 237References 237

30 Catalytic Asymmetric (4 + 3) Cycloadditions Using Allenamides 239Yun-Fei Du and Richard P. HsungIntroduction and Background 239Strategy 240Results 240Conclusion 242CV of Yun-Fei Du 246CV of Richard P. Hsung 246References 246

XII Contents

31 Application of the Achmatowicz Rearrangement for the Synthesis ofOligosaccharides 249Michael F. Cuccarese and George A. O’DohertyIntroduction 249De novo Approach to Carbohydrates 249An Iterative Pd-Catalyzed Glycosylation and BidirectionalPostglycosylation 251Application to the Synthesis of the Anthrax Tetrasaccharide 251CV of Michael F. Cuccarese 255CV of George A. O’Doherty 258References 258

32 Asymmetric C–C Bond Formation Using Chiral Phosphoric Acid 261Takahiko AkiyamaBackground 261Results 261

a) Mannich and Related Reactions 261b) Cycloaddition Reactions 262c) Transfer Hydrogenation Reactions 263d) Friedel-Crafts Alkylation Reaction 264e) Desymmetrization reaction 264

Conclusions and Future Perspectives 265CV of Takahiko Akiyama 266References 266

33 Asymmetric C–H Bond Functionalization 267Masayuki Wasa, Kelvin S. L. Chan, and Jin-Quan YuBackground 267Results 267

a) Diastereoselective C–H Functionalization 267b) Enantioselective C–H Functionalization 269

Conclusions and Future Perspectives 271CV of Masayuki Wasa 271CV of Kelvin S. L. Chan 272CV of Jin-Quan Yu 272References 272

34 Asymmetric C–C Bond Formation Using Chiral Guanidine Catalysts 273Masahiro TeradaBackground 273Catalyst Design and Results 273

a) Design of Novel Axially Chiral Guanidine Base Catalysts 273b) Type I Axially Chiral Guanidine Catalysts (Nine-Membered

Ring) 275

Contents XIII

c) Type II Axially Chiral Guanidine Catalysts (Seven-MemberedRing) 276

CV of Masahiro Terada 278References 278

35 Enantioselective Synthesis of Lactones via Rh-Catalyzed KetoneHydroacylation 279Matthew M. Coulter and Vy M. DongBackground and Introduction 279Strategy and Results 279Conclusions and Future Directions 283CV of Vy M. Dong 283CV of Matthew M. Coulter 284References 284

36 Radical Haloalkylation 285Armen ZakarianCV of Armen Zakarian 290References 291

37 Asymmetric Hydrovinylation of Alkenes 293T. V. (Babu) RajanBabuIntroduction 293New Protocols for the Heterodimerization of Ethylene/Propylene andVinylarenes, 1,3-Dienes, and Norbornene 293Catalytic Asymmetric Hydrovinylation Reactions: Effects of HemilabileLigands 295All-Carbon Quaternary Centers via Catalytic Asymmetric HV 295Hydrovinylation (HV) of 1,3-Dienes and Asymmetric Variations 296Asymmetric Hydrovinylation of Unactivated Linear 1,3-Dienes UsingCo(II) Catalysis 296Scope and Applications of Hydrovinylation Reactions: ExocyclicStereocontrol 296A Stereoselective Route to either Steroid-C20(S) or -C20(R)Derivatives 298Asymmetric Hydrovinylation of Strained Alkenes 298Conclusions and Future Perspectives 300CV of T. V. (Babu) RajanBabu 300References 301

38 Heterocycle Construction via Asymmetric Rhodium-CatalyzedCycloadditions 303Kevin M. Oberg and Tomislav RovisBackground 303Strategy 304

XIV Contents

Results 305Application to Other Reactions 306Conclusion and Future Perspectives 307CV of Tomislav Rovis 307CV of Kevin M. Oberg 307References 307

39 N-Heterocyclic Carbene-Catalyzed Aldol Desymmetrizations 309Karl A. Scheidt, Eric M. Phillips, and Julien Dugal-TessierIntroduction 309Strategy and Results 309Application to the Syntheses of Bakkenolides I, J, and S 312Conclusion 314CV of Karl A. Scheidt 315CV of Eric M. Phillips 315CV of Julien Dugal-Tessier 315References 316

40 Strategies for the Asymmetric Total Synthesis of Natural Products:‘‘Chiral Pool’’ versus Chiral Catalysts 317Karl GademannIntroduction 317Catalytic Stereoselective Total Synthesis 317Natural Product Synthesis Starting from Chiral, Nonracemic StartingMaterials 320Conclusion 321CV of Karl Gademann 321References 322

41 Dynamic Kinetic Asymmetric Transformations Involving Carbon–CarbonBond Cleavage 323Andrew T. Parsons and Jeffrey S. JohnsonBackground 323Donor–Acceptor Cyclopropanes as DYKAT Substrates 323Lewis Acid Catalysis 323Palladium Catalysis 326Deracemization of Tertiary Propargyl-Allyl Alcohols viaRhodium-Catalyzed Sequential Rearrangement/EnantioselectiveConjugate Addition 329Conclusion 329CV of Andrew Parsons 331CV of Jeffrey Johnson 331References 331

Contents XV

42 Iron-Catalyzed Allylic Substitutions 333Markus Jegelka and Bernd PlietkerAllylic Substitutions Catalyzed by the Hieber-Anion[Fe(CO)3(NO)]− 333Allylic Substitutions Catalyzed by Fe2(CO)9 338CV of Markus Jegelka 340CV of Bernd Plietker 340References 341

43 Asymmetric Conia-ene Carbocyclizations 343Filippo Sladojevich and Darren J. DixonIntroduction and Background: the Conia-ene Reaction 343Strategy: Organo/Metal Cooperative Catalysis 343Results 344CV of Filippo Sladojevich 349CV of Darren J. Dixon 349References 350

44 Tactics and Strategies in the Total Synthesis of Chlorosulfolipids 353Christian Nilewski and Erick M. CarreiraBackground 353Stereoselective Synthesis of vic-Dichloride Fragments 353Total Synthesis of Hexachlorosulfolipid 357Conclusions 360CV of Christian Nilewski 360CV of Erick M. Carreira 360References 360

45 Linear Free Energy Relationships (LFERs) in Asymmetric Catalysis 363Elizabeth N. Bess and Matthew S. SigmanIntroduction and Background 363Hammett Electronic Parameters and Their Application to(salen)Mn(III)-Catalyzed Asymmetric Epoxidation Reactions 364Relating Brønsted Acidity to Enantiomeric Ratio in an AsymmetricHydrogen-Bond-Catalyzed Diels-Alder Reaction 365An LFER Describing the Influence of Steric Bulk in aNozaki–Hiyama–Kishi Asymmetric Allylation of Acetophenone 367Correlating Quadrupole Moment to Enantioselectivity inCation-π-Mediated Asymmetric Polycyclization 367Simultaneously Correlating Hammett and Charton Parameters toEnantioselectivity in Two-Dimensional Free Energy Relationships 368Conclusions 369CV of Elizabeth Bess 369CV of Matt Sigman 369References 370

XVI Contents

46 Asymmetric Diamination of Alkenes 371Jose A. Souto and Kilian MunizIntroduction and Background 371Strategy 371Results 371CV of Jose Souto 374CV of Kilian Muniz 375References 375

47 Enzymatic Asymmetric Synthesis of Tertiary Alcohols 377Michael RichterIntroduction 377YerE–a Unique ThDP-Dependent Enzyme 377Hydroxynitrile Lyases 379Conclusion 380CV of Michael Richter 381References 381

48 Oxidative Dearomatization and Organocatalytic Desymmetrization 383Alice E. Williamson and Matthew J. GauntIntroduction 383Desymmetrization of Cyclohexadienones 383A One-Pot Oxidative Dearomatization and CatalyticDesymmetrization 384Oxo- and Aza-Michael Additions 384Further One-Pot Methods for Oxidative Dearomatization and CatalyticDesymmetrization 386Alkylative Dearomatization 386Summary 389CV of Matthew J. Gaunt 389CV of Alice E. Williamson 390References 390

49 Total Synthesis of All (–)-Agelastatin Alkaloids 391Mohammad Movassaghi and Sunkyu HanIntroduction 391Biosynthetically Inspired Plan for Total Synthesis 391Total Synthesis of the Agelastatin Alkaloids 393CV of Mohammad Movassaghi 395CV of Sunkyu Han 396References 396

Index 397

XVII

List of Contributors

Takahiko AkiyamaGakushuin UniversityDepartment of Chemistry1-5-1 MejiroToshima-kuTokyo 171-8588Japan

Iuliana AtodireseiInstitute of Organic ChemistryRWTH Aachen UniversityLandoltweg 1 52074AachenGermany

Phil S. BaranThe Scripps Research InstituteDepartment of chemistry10550 N. Torrey Pines RoadSan DiegoCA 92037USA

Santiago BarrosoUniversity of GroningenDepartment of Bio OrganicChemistryStratingh Institute for ChemistryNijenborgh 49747 GroningenThe Netherlands

Elizabeth N. BessUniversity of UtahDepartment of Chemistry315 S. 1400 E.Salt Lake CityUtah, 84112-0850USA

Jeffrey W. BodeLaboratorium fur OrganischeChemieDepartment of Chemistry andApplied BiosciencesETH Zurich. Wolfgang PauliStrasse 108093 ZurichSwitzerland

Alexandria P. BrucksColumbia University3000 BroadwayNew YorkNY 10027USA

Noah Z. BurnsThe Scripps Research InstituteDepartment of chemistry10550 N. Torrey Pines RoadSan DiegoCA 92037USA

XVIII List of Contributors

Erick M. CarreiraETH ZurichLaboratorium fur OrganischeChemieHCI H3358093 ZurichSwitzerland

Kelvin S. L. ChanThe Scripps Research InstituteDepartment of Chemistry10550 N. Torrey Pines RoadLa JollaCA 92037USA

Mathias ChristmannDepartment of ChemistryTechnical University ofDortmundOtto-Hahn-Str. 644227 DortmundGermany

Nicolai CramerLaboratory of AsymmetricCatalysis and SynthesisInstitute of Chemical Sciencesand EngineeringEcole Polytechnique Federale deLausanne1015 LausanneSwitzerland

Matthew M. CoulterUniversity of TorontoDepartment of Chemistry80 St. George StreetTorontoON M5S 3H6Canada

Michael F. CuccareseNortheastern UniversityDepartment of Chemistry andChemical Biology360 Huntington AveBostonMA 02115USA

Darren J. DixonUniversity of OxfordDepartment of ChemistryMansfield Road 12OxfordOX1 3TAUK

Vy M. DongUniversity of TorontoDepartment of Chemistry80 St. George StreetTorontoON M5S 3H6Canada

Timothy J. DonohoeUniversity of OxfordDepartment of ChemistryChemistry Research LaboratoryMansfield RoadOxfordOX1 3TAUK

Yun-Fei DuTianjin UniversitySchool of Pharmaceutical Scienceand Technology92 Weijin Road Nankai DistrictTianjin 300072China

List of Contributors XIX

Julien Dugal-TessierNorthwestern UniversityDepartment of Chemistry2145 Sheridan RoadEvanstonIL 60208USA

Antonio M. EchavarrenInstitute of Chemical Research ofCatalonia (ICIQ)Av. Paisos Catalans 1643007 TarragonaSpain

Kurt FaberUniversity of GrazDepartment of ChemistryOrganic & Bioorganic ChemistryHeinrichstrasse 288010 GrazAustria

Umar FaridCardiff UniversitySchool of ChemistryPark PlaceMain BuildingCardiffWales CF10 3ATUK

Karl GademannUniversity of BaselDepartment of ChemistrySwiss National Centre ofCompetence in ResearchChemical BiologySt. Johanns-Ring 194056 BaselSwitzerland

Tanja GaichLeibniz Universitat HannoverInstitute of Organic ChemistrySchneiderberg 1B30167 HannoverGermany

and

University of ViennaDepartment of SyntheticChemistryInstitute for Organic ChemistryWahringer Strasse 381090 ViennaAustria

Matthew J. GauntUniversity of CambridgeDepartment of ChemistryLensfield RoadCambridgeCB2 1EWUK

Ryan GilmourETH ZurichLaboratorium fur OrganischeChemieWolfgang-Pauli-Str. 108093 ZurichSwitzerland

Melanie HallUniversity of GrazDepartment of ChemistryOrganic & Bioorganic ChemistryHeinrichstrasse 288010 GrazAustria

XX List of Contributors

Sunkyu HanMassachusetts Institute ofTechnologyDepartment of Chemistry77 Massachusetts AvenueCambridge, MA 02139USA

Tobias HarschneckOrganic ChemistryBergische Universtat WuppertalGaußstr. 2042119 WuppertalGermany

Yujiro HayashiTokyo University of ScienceDepartment of IndustrialChemistry1-3 KagurazakaTokyo 162-8601Japan

Stefan HechtHumboldt-Universitat zu BerlinDepartment of ChemistryLaboratory of Organic Chemistryand Functional MaterialsBrook-Taylor-Strasse 212489 BerlinGermany

Martin HiersemannCardiff UniversityPhysical Organic ChemistryCentrePark PlaceCF11 3AT CardiffUK

Lukas HintermannTechnische Universitat MunchenDepartment ChemieLichtenbergstr. 485747Garching bei. MunchenGermany

Richard P. HsungUniversity of WisconsinPharmaceutical Sciences andChemistry7111 Rennebohm HallMadisonWI 53705-2222USA

Nuria HuguetInstitute of Chemical Research ofCatalonia (ICIQ)Av. Paisos Catalans 1643007 TarragonaSpain

Tsubasa InokumaKyoto UniversityGraduate School ofPharmaceutical SciencesYoshida

and

Sakyo-kuKyoto 606-8501Japan

Hayato IshikawaTokyo University of ScienceDepartment of IndustrialChemistry1-3 KagurazakaTokyo 162-8601Japan

List of Contributors XXI

Markus JegelkaInstitut fur Organische ChemieUniversitat StuttgartPfaffenwaldring 55DE–70569 StuttgartGermany

Jeffrey S. JohnsonDepartment of ChemistryUniversity of North CarolinaChapel HillNC 27510USA

Richard M. KelloggSyncom BVKadijk 39747 AT GroningenThe Netherlands

Stefan F. KirschOrganic ChemistryBergische Universitat WuppertalGaußstr. 2042119 WuooertalGermany

Michael J. KrischeThe University of Texas at AustinDepartment of Chemistry andBiochemistryCenter for Green Chemistry andCatalysis105 E 24th st. (A5300)AustinTX 78712USA

Wolfgang KroutilUniversity of GrazDepartment of ChemistryOrganic & Bioorganic ChemistryHeinrichstrasse 288010 GrazAustria

Benjamin ListMax-Planck-Institut furKohlenforschungKaiser-Wilhelm-Platz 145470 Mulheim an der RuhrGermany

David W. C. MacMillanPrinceton UniversityDepartment of ChemistryFrick LaboratoryWashington RoadPrincetonNJ 08544USA

Jessada MahatthananchaiLaboratorium fur OrganischeChemieDepartment of Chemistry andApplied BiosciencesETH Zurich. Wolfgang PauliStrasse 108093 ZurichSwitzerland

Manuel MahlauMax-Planck-Institut furKohlenforschungKaiser-Wilhelm-Platz 145470 Mulheim an der RuhrGermany

Martin E. MaierUniversitat TubingenInstitut fur Organische ChemieAuf der Morgenstelle 1872076 TubingenGermany

XXII List of Contributors

Stefanie MeschUniversity of OxfordDepartment of ChemistryChemistry Research LaboratoryMansfield RoadOxfordOX1 3TAUK

Adriaan J. MinnaardUniversity of GroningenDepartment of Bio OrganicChemistryStratingh Institute for ChemistryNijenborgh 49747 GroningenThe Netherlands

Joseph MoranThe University of Texas at AustinDepartment of Chemistry andBiochemistryCenter for Green Chemistry andCatalysis105 E 24th st. (A5300)AustinTX 78712USA

Mohammad MovassaghiMassachusetts Institute ofTechnologyDepartment of Chemistry77 Massachusetts AvenueCambridge, MA 02139USA

Johann MulzerLeibniz Universitat HannoverInstitute of Organic ChemistrySchneiderberg 1B30167 HannoverGermany

and

University of ViennaDepartment of SyntheticChemistryInstitute for Organic ChemistryWahringer Strasse 381090 ViennaAustria

Kilian MunizInstitute of Chemical Research ofCatalonia (ICIQ)Av. Paısos Catalans 1643007 TarragonaSpain

and

Catalan Institution for Researchand Advanced Studies (ICREA)Pg. Lluıs Companys 2308010 BarcelonaSpain

Vaidotas NavickasUniversitat TubingenInstitut fur Organische ChemieAuf der Morgenstelle 1872076 TubingenGermany

List of Contributors XXIII

Christian NilewskiETH ZurichLaboratorium fur OrganischeChemieHCI H3358093 ZurichSwitzerland

Kevin M. ObergColorado State UniversityDepartment of ChemistryCO 80523USA

George A. O’DohertyNortheastern UniversityDepartment of Chemistry andChemical Biology360 Huntington AveBostonMA 02115USA

Martin OestreichTechnische Universitat BerlinInstitut fur ChemieStrass des 17. juni 11510623 BerlinGermany

Andrew T. ParsonsDepartment of ChemistryUniversity of North CarolinaChapel HillNC 27510USA

Bernd PlietkerInstitut fur Organische ChemieUniversitat StuttgartPfaffenwaldring 55DE–70569 StuttgartGermany

Eric M. PhillipsNorthwestern UniversityDepartment of Chemistry2145 Sheridan RoadEvanstonIL 60208USA

T. V. (Babu) RajanBabuThe Ohio State UniversityDepartment of Chemistry100 West 18th AvenueColumbusOH 43210USA

Corey M. ReevesCalifornia Institute of TechnologyDivision of Chemistry andChemical Engineering1200 E. California Blvd.PasadenaCA 91125USA

Julia RehbeinCardiff UniversityPhysical Organic ChemistryCentrePark PlaceCF11 3AT CardiffUK

Sebastian RendlerSyngenta Crop ProtectionMunchwilen AGSchaffhauserstrasse4332 SteinSwitzerland

XXIV List of Contributors

Michael RichterEmpa. Swiss Federal Laboratoriesfor Materials Science andTechnologyLaboratory for BiomaterialsLerchenfeldstr. 59014 St. GallenSwitzerland

Tomislav RovisColorado State UniversityDepartment of ChemistryCO 80523USA

Julian H. RowleyWestCHEM, Department of Pureand Applied ChemistryThomas Graham BuildingUniversity of Strathclyde295 Cathedral StreetGlasgowG1 1XLUK

Magnus RuepingInstitute of Organic ChemistryRWTH Aachen UniversityLandoltweg 1 52074AachenGermany

Karl A. ScheidtNorthwestern UniversityDepartment of Chemistry2145 Sheridan RoadEvanstonIL 60208USA

Tobias SeiserLaboratory of AsymmetricCatalysis and SynthesisInstitute of Chemical Sciencesand EngineeringEcole Polytechnique Federale deLausanne1015 LausanneSwitzerland

Matthew S. SigmanUniversity of UtahDepartment of Chemistry315 S. 1400 E.Salt Lake CityUtah, 84112-0850USA

Filippo SladojevichUniversity of OxfordDepartment of ChemistryMansfield Road 12OxfordOX1 3TAUK

Christof SparrETH ZurichLaboratorium fur OrganischeChemieWolfgang-Pauli-Str. 108093 ZurichSwitzerland

Brian M. StoltzCalifornia Institute of TechnologyDivision of Chemistry andChemical Engineering1200 E. California Blvd.PasadenaCA 91125USA

List of Contributors XXV

Scott A. SnyderColumbia University3000 BroadwayNew YorkNY 10027USA

Jose A. SoutoInstitute of Chemical Research ofCatalonia (ICIQ)Av. Paısos Catalans 1643007 TarragonaSpain

and

Catalan Institution for Researchand Advanced Studies (ICREA)Pg. Lluıs Companys 2308010 BarcelonaSpain

Yoshiji TakemotoKyoto UniversityGraduate School ofPharmaceutical SciencesYoshidaSakyo-kuKyoto 606-8501Japan

Masahiro TeradaTohoku UniversityDepartment of ChemistryGraduate School of Science6-3 Aza-Aoba, Aramaki, Aoba-kSendai 980-8578Japan

Nicholas C. O. TomkinsonWestCHEM, Department of Pureand Applied ChemistryThomas Graham BuildingUniversity of Strathclyde295 Cathedral StreetGlasgowG1 1XLUK

Oliver TrappRuprecht-Karls-UniversitatHeidelbergOrganisch-Chemisches InstitutIm Neuenheimer Feld 27069120 HeidelbergGermany

Uxue UriaInstitute of Organic ChemistryRWTH Aachen UniversityLandoltweg 1 52074AachenGermany

Philipp ViehmannHumboldt-Universitat zu BerlinDepartment of ChemistryLaboratory of Organic Chemistryand Functional MaterialsBrook-Taylor-Strasse 212489 BerlinGermany

Mei-Xiang WangKey Laboratory of BioorganicPhosphorous Chemistry andChemicalBiology (Ministry of Education),Department of ChemistryTsinghua University100084 BeijingChina

XXVI List of Contributors

Qian WangInstitute of Chemical Sciencesand EngineeringEcole Polytechnique Federale deLausanneEPFL-SB-ISIC-LSPNBCH5304 (Bat BCH)CH-1015 LausanneSwitzerland

Masayuki WasaThe Scripps Research InstituteDepartment of Chemistry10550 N. Torrey Pines RoadLa JollaCA 92037USA

Andreas WeickgenanntWestfalischeWilhelms-Universitat MunsterOrganisch-Chemisches InstitutCorrensstraße 4048149 MunsterGermany

Alice E. WilliamsonUniversity of CambridgeDepartment of ChemistryLensfield RoadCambridgeCB2 1EWUK

Thomas WirthCardiff UniversitySchool of ChemistryPark PlaceMain BuildingCardiffWales CF10 3ATUK

Jin-Quan YuDepartment of ChemistryThe Scripps Research Institute10550 N. Torrey Pines RoadLa JollaCalifornia 92037USA

Armen ZakarianUniversity of California at SantaBarbaraDepartment of Chemistry andBiochemistrySanta BarbaraCA 93106-9510USA

Jieping ZhuInstitute of Chemical Sciencesand EngineeringEcole Polytechnique Federale deLausanneEPFL-SB-ISIC-LSPNBCH5304 (Bat BCH)CH-1015 LausanneSwitzerland

Lucie E. ZimmerETH ZurichLaboratorium fur OrganischeChemieWolfgang-Pauli-Str. 108093 ZurichSwitzerland