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Tetrahedron: Asymmetry Vol. 25, No. 3, 2014

Contents

COMMUNICATION

Asymmetric alkyne addition to aldehydes catalyzed by Schiff bases made from 1,10-bi-2-naphthol and chiralbenzylic amines

pp 199–201

Cen Chen, Qingfei Huang, Sheng Zou, Lei Wang, Bao Luan, Jin Zhu, Qiwei Wang*, Lin Pu*

Ph +

1. 6 (0.1 equiv)rt, 1 h

Ph

OH

R

ZnEt2

2. RCHO

0 °C, 24 h

OH

OH

N

N

(R)

(S)

(S)

up to 83%, 85% ee

4 equiv 4 equiv

ARTICLES

A facile chiral pool synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O pp 203–211

K. Vamshikrishna, G. Srinu, P. Srihari*

O

O

HO

OH

OH

decarestrictine-D

L-(+)-diethyl tartrate

O

O

O

OH

O

O

O

O

HO

OH

OH

decarestrictine-O

OH

O O

OH

O O

OH

O

Enantioselective Michael addition of cyclic ketones to nitroolefins catalyzed by a novel fluorine-insertion organocatalyst pp 212–218

Yanan Wang, Min Jiang, Jin-Tao Liu*

R1

NO2+

O1-F (10 mol% )

CF3COOH (0 or 10 mol%)

neat, rt

O

NO2

R1

2 34, up to 99% ee

up to 99:1 drR1 = aryl, alkyl

n = 2, 3, 4

( )n

( )n

NH

N

F

1-F

Contents lists available at ScienceDirect

Tetrahedron: Asymmetry

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

Limonene oxide derived aziridinyl alcohols as highly efficient catalysts for asymmetric additions of organozincspecies to aldehydes

pp 219–223

Michał Rachwalski*

Ph +catalyst, Et2Zn

THFPh

OH

R

catalyst, Et2Zn

toluene R

OH

R H

O

R H

O

yields: 88-97%ee`s: 86-95%

catalysts:

aziridines:

N

H

Me

HN

H

Pri

H N

H

H

PriN

H

Ph

H

Me OH

N

R2

R1

Enantiodifferentiation of the antitumor alkaloid crispine A using the NMR chiral solvating agents (R)- and (S)-BINOL pp 224–228

Francisco Yuste*, Rubén Sánchez-Obregón, Eduardo Díaz, Mario A. García-Carrillo

OH

OH N

MeO

MeO

H7R S

H-7 signals in the 1H NMR spectra of a 93:7 sample of crispine A complexed with five equivalents of (S)-BINOL in CDCl3.

Conformational behavior of peptides containing residues of 3-azetidinesulfonic (3AzeS) and4-piperidinemethanesulfonic (4PiMS) acids

pp 229–237

Oleksandr O. Grygorenko*, Sergey Zhersh, Bohdan V. Oliinyk, Oleg V. Shishkin, Andrey A. Tolmachev

N

O

H

S

O

O N

O

H

S

O

O

axial chirality

3AzeS 4PiMS

Evaluating dynamic kinetic resolution strategies in the asymmetric hydrosilylation of cyclic ketimines pp 238–244

Simon Jones*, Peichao Zhao

NBn

Me

HSiCl3, CH2Cl2

10 mol% catalyst

NHBn

Me

N

N

Me

O

N

OH

Ph

Ph

catalyst

iv

Highly enantioselective Friedel–Crafts alkylation of indole with electron deficient trans-b-nitroalkenes usingZn(II)–oxazoline–imidazoline catalysts

pp 245–251

Mohammad Shahidul Islam*, Abdullah M. A. Al Majid*, Zeid Abdullah Al-Othman, Assem Barakat

NH

+

NH

Cat* 10 mol%NO2

NO2

H

R1

R1

O

N N

N

Zn2+

OTfTfO

R

37 - 95% yieldup to 99% ee

Cat*

iPr iPrtoluene, 0 oC

A convenient procedure for the synthesis of chiral 6,7-dihydroxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones

pp 252–257

Yakdhane Kacem, Béchir Ben Hassine*

RN

N

O

H

H

NH2

+

OOHO

O ON

N

OH

OH

O

O

H

HH

HR

NH

1) PTSA, EtOH, 80 °C

2) MeOH-HCl, 0 °C

>99% deR = Me, i-Pr, i-Bu, Bn, CH2OH, CH2-CH2SMe

Rh-catalyzed asymmetric hydrogenation using a furanoside monophosphite second-generation ligand library:scope and limitations

pp 258–262

Sabina Alegre, Elisabetta Alberico, Oscar Pàmies, Montserrat Diéguez*

OO

O

O

OO

P

O

O

OO

O

O

O

OP

O

O

Me

R

R= Alkyl, aryl

CO2MeR2

R1

Rh/L*

10 bar H2CO2MeR2

R1

*

R1 = H, Ph

R2

= CH2CO2Me, NHAc

ee's up to 99.9%

NHAcR

Rh/L*

10 bar H2NHAcR

*

R = aryll ee's up to 67%

Convergent synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonellaenterica O44

pp 263–267

Debashis Dhara, Pintu Kumar Mandal*, Anup Kumar Misra*

HO

O

O

HO

OH

HO

O

OH

O

HO

O

NH2

O

NHAc

OH

HO

O

O

HO

HO OH

O

O

NHAc

OH

HO

HO

v

Sharpless asymmetric dihydroxylation as the key step in the enantioselective synthesis of spirocyclic r1 receptor ligands pp 268–277

Katharina Holl, Dirk Schepmann, Constantin Gabriel Daniliuc, Bernhard Wünsch*

Br Br

OH

OH

O

F

N

Bn

AD-mix-β5 steps

97.6 % ee

Ki(σ1) = 1.8 nM

eudismic ratio: 8

σ1:σ2 selectivity: >660

Application of chiral N,N0-dialkyl-1,2-cyclohexanediamine derivatives in asymmetric copper(II)-catalyzed Henryreactions

pp 278–283

Zhao Chunhong, Fei Liu, Shaohua Gou*

Enzymatic asymmetric synthesis of the silodosin amine intermediate pp 284–288

Robert C. Simon, Johann H. Sattler, Judith E. Farnberger, Christine S. Fuchs, Nina Richter, Ferdinand Zepeck,Wolfgang Kroutil*

NO

CNR

R = (CH2)3OBz

NNH2

CNR

ωTA, PLP

alanine pyruvate(recycling/removal)

(R)

up to >97% e.e.up to >97% conv.

OTHER CONTENTS

Stereochemistry abstracts pp A53–A78

Cumulative author index p I

*Corresponding author

vi

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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