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Tetrahedron: Asymmetry Vol. 24, No. 19, 2013

Contents

REPORT

Oxazolidinones as chiral auxiliaries in asymmetric aldol reactions applied to total synthesis pp 1149–1188

Majid M. Heravi*, Vahideh Zadsirjan

R2

NO

O

R1O

+

Asymmetric Aldol reaction

R3 H

O

O

OO

MeO

OMe

H

HO

OH

OHHO

MeO

OMeO

OMe

NH

OO

O

MeO

CONH2

HON

N

N N

NH2

HN

NH

O

OMe

O

O

HO

O

OOHHOH

OO

OH

O

OOHNO

N

ONO

S

NHN

O

HOOMe O

O

N

MeO

MeOH

OH

COMMUNICATION

Chiral bifunctional organocatalysts bearing a 1,3-propanediamine unit for the aza-MBH reaction pp 1189–1192

Shuichi Hirata, Kouichi Tanaka, Katsuya Matsui, Fernando Arteaga Arteaga, Yasushi Yoshida, Shinobu Takizawa*,Hiroaki Sasai*

OH

OH

N N

Bn

ARTICLES

New chiral iodooxazoline catalysts for the I(III)-mediated a-tosyloxylation of ketones: refining thestereoinduction model

pp 1193–1197

Marie-Ève Thérien, Audrey-Anne Guilbault, Claude Y. Legault*

(R)-productONH

I

OH

Me

TsO-

TsO-

IN

O

Contents lists available at ScienceDirect

Tetrahedron: Asymmetry

journal homepage: www.elsevier .com/locate / tetasy

Molecular dynamics study of the influence of solvents on the chiral discrimination of alanine enantiomersby b-cyclodextrin

pp 1198–1206

Elena Alvira*

waterL DL D

A concise and stereoselective chemoenzymatic synthesis of Sitophilate, the male-produced aggregation pheromoneof Sitophilus granarius (L.)

pp 1207–1211

Silvana P. Ravía, Mariela Risso, Santiago Kröger, Silvana Vero, Gustavo A. Seoane, Daniela Gamenara*

O

O O

fungal reductionO

OH O

i) Mitsunobu inversion

ii) enzymatic transesterificationO

OH O

Practical synthesis of diastereoisomers by a temperature-guided reversal of diastereoselectivity in thedesymmetrization of meso-bridged anhydrides with a chiral oxazolidin-2-one

pp 1212–1217

Narendra R. Chaubey, Amey P. Wadawale, Sunil K. Ghosh*

Y

X

CO2Me

NO

O O

Y

X

MeO2C ON

O

O

Y

X

O

HH

O

O

Ph

Ph

LiNO

Ph

O

Ph LiNO

Ph

O

Ph

PhPh-78oC

then CH2N228oC

then CH2N2

X = CH2/CH2CH2; Y = CH2CH2/CH=CH

Self-assembly of an organocatalyst for the enantioselective synthesis of Michael adducts and a-aminoxyalcohols in a nonpolar medium

pp 1218–1224

Ayhan Sıtkı Demir, Sinan Basceken*

N

N

N

SCF3

CF3

NH O

O

H

H

H

nonpolar solvent

catalyst:

Host

Guest

Ph

O+R

O

R1

(R)R

O

R1N NHO

Phnonpolar solvent

Michael reaction

α-aminoxylation

NO2

(S)+

O

R1

(R) NO2

O

R1

-30 oC

R2

R2

syn

rt

Yields= 54-77%ee= 90-98%

Yields= 60-85%ee= 94-99%NaBH4

EtOH O(R)HO

R1

NH

Ph

R= H

iv

The combi-CLEA approach: enzymatic cascade synthesis of enantiomerically pure (S)-mandelic acid pp 1225–1232

Andrzej Chmura, Sven Rustler, Monica Paravidino, Fred van Rantwijk, Andreas Stolz, Roger A. Sheldon*

O

H

CN

OH

COO-NH4+

OH

CONH2

OH

(S)-HnL

HCN

NLase

2 H2O

> 90% final yield> 99% ee (S)

amidaseH2O

> 99% ee (S)

+

Reactions of carbon nucleophiles with 2,2,3-trisubstituted ethynylaziridines pp 1233–1239

Brandon T. Kelley, Madeleine M. Joullié*

A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines

pp 1240–1246

Dmitry A. Gruzdev, Evgeny N. Chulakov, Galina L. Levit*, Marina A. Ezhikova, Mikhail I. Kodess, Victor P. Krasnov

CH2Cl2

fluorinated: s 20-53

non-fluorinated: s 12-19

(S,S)-amides

fluorinated: s 1.7-13

non-fluorinated: s 6.2-19

(0.5 equiv.)

R = Ph, iPr

X

NH

Me

Y

Y

Me

COCl

MeO

X

N

Me

Y

Y

O

Me

OMePhthN COCl

R (0.5 equiv.)

(S,S)-amides

X

N

Me

Y

Y

O

NPhth

R

CH2Cl2

rac

X = O, CH2Y = F, H

Autoxidation of a tetracyclic lactam and its conversion to an enantiopure tertiary alcohol pp 1247–1251

El _zbieta Wojaczynska*, Ilona Turowska-Tyrk

N

HN

ON

HN

O [H] N

HN

ON

HN

OHOO

[O]

2

[H]

v

OTHER CONTENTS

Stereochemistry abstracts pp A303–A318

Tetrahedron: Asymmetry Reports pp I–IV

Cumulative author index pp V–VII

*Corresponding author

Available online at www.sciencedirect.com

ScienceDirect

Indexed/Abstracted in: Beilstein, BIOSIS Previews, Chemical Abstracts, Current Contents: Physical, Chemical and EarthSciences, Derwent Biotechnology Abstracts, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, PASCAL, ResearchAlert, Science Citation Index, SciSearch. Also covered in the abstract and citation database Scopus®. Full text available onScienceDirect®

ISSN 0957-4166

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