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Tetrahedron: Asymmetry Vol. 24, No. 12, 2013

Contents

ARTICLES

Asymmetric synthesis of 1,2,3-trisubstituted indanes via an enantioselective copper(II)-catalyzed asymmetric nitroaldolreaction followed by an intramolecular Michael cyclization

pp 699–705

Hongling Yuan, Junhao Hu, Yuefa Gong*

DIPEA (0.1 equiv),THF, -20 °C

CHO

EWG

+ CH3NO2CH3NO2

NO2

OH

EWG

R R

EWG

R

OH

NO25 mol% L1 /

R= H, NO2, 3,4-OCH2O-; EWG= COOR, COAr, CN

NNH

H

L1 =

10 examples,yields:40-92%dr: 69:31-87:13up to 97% ee

Cu(OAc)2·H2O

Chiral benzimidazole-derived mono azacrowns: synthesis and enantiomer recognition studies with chiral amines andtheir ammonium salts

pp 706–712

Anita Pandey, Hasan Mohammed, Anil Karnik*

mono aza-15-crown-5(S)-(-)-2-(α-hydroxyethyl) benzimidazole

NH

N

OH

HCH3

+OTs

O O O

1 2

TsO

N

OO

O

H

ON

CH3

dry THF, NaH

reflux, 8 hrs.

New chiral polyfunctional cyclobutane derivatives from ())-verbenone: possible surfactant behaviour pp 713–718

Jimena Ospina, Alessandro Sorrenti, Ona Illa, Ramon Pons*, Rosa M. Ortuño*

NH2

CO2HH

HNH

O

Contents lists available at SciVerse ScienceDirect

Tetrahedron: Asymmetry

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

Chiral fluoroacetic acid: synthesis of (R)- and (S)-[2H1]-fluoroacetate in high enantiopurity pp 719–723

Rudy D.P. Wadoux, Xiaowei Lin, Neil S. Keddie, David O�Hagan*

O

O

F

HD

Na

O

O

F

DH

Na

(S)-[2H1]-fluoroacetate 1b(R)-[2H1]-fluoroacetate 1a

Stereoselective total synthesis of Ieodomycin A and B pp 724–728

Emmadi Narender Reddy, Atmakur Krishnaiah*, Tadikamalla Prabhakar Rao

HO O

OH

OH

COOMe

OH

Ieodomycin A 2

O

OH

O

Ieodomycin B 1

geraniol

Synthesis of a chiral N-heterocyclic carbene bearing a m-terphenyl-based phosphate moiety as an anionic N-substituentand its application to copper-catalyzed enantioselective boron conjugate additions

pp 729–735

Tomohiro Iwai, Yuki Akiyama, Masaya Sawamura*

OMe

Cu–1a (3.0 mol %)KOtBu (30 mol %)

pinB–Bpin (1.1 eq)MeOH (2.0 eq)THF, –55 ºC, 24 h

O

Ph

OMe

O

Ph

Bpin

89% ee86% yield

anionic coordination site

electronicallytunable substituent

derived from achiral diamine

environment

1) stereogenic centers

2) global chiral

3) phosphate-type

4) sterically and N N

R3R2

O

OP

O

O

R1

R4

R5

1a: R1=2,4,6-Me3-C6H2, R2 = R

3 = Ph, R

4 = R

5 = H

Modular bipyridine ligands coupled with Cinchona alkaloids for Cu(II)-catalyzed asymmetric Henry reactions pp 736–743

Ming Liu, Shijun Ma, Zhiqing Tian, Hao Wu, Lulu Wu, Xiufang Xu, Yaodong Huang*, Yongmei Wang*

R H

O

+ CH3NO2 R

OH

NO2CuCl2•2H2O (5 mol%)

EtOH (0.5 mL), 0° C, 24 h

N

O

N

O

N

N

1a 6 mol%

yeild : up to 89%ee : up to 92%

1a

A new series of bipyridine ligands have been used as ligands in the asymmetric Henry reaction for the first time.

iv

Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives

pp 744–749

Alejandro A. Orden, Joerg H. Schrittwieser, Verena Resch, Francesco G. Mutti, Wolfgang Kroutil*

O NH2

ω-transaminaseMeO MeO

R RD-AlaN

OH

MeO

(1S,3R)

R (S)

(R)

R = H, OMe(R)

steps

AraBOX and XyliBOX based catalysts for cyclopropanations, Diels Alder cycloadditions and allylic additions pp 750–757

David Kellehan, Fiona Kirby, David Frain, Antonio M. Rodríguez-García, José I. García, Patrick O�Leary*

ON N

O

Me Me

ON N

O

Ph Ph

ON N

O

Ph Ph

+ N2CHCO2Et

CO2Et

Cu(OTf)2

ligand

de up to 26%ee up to 70%

Total synthesis of the 2,6-disubstituted piperidine alkaloid ())-andrachcinidine pp 758–763

Palakodety Radha Krishna*, Bonepally Karunakar Reddy

NH

OOH

(-)-andrachcinidine

asymmetric allylation aza-Michael addition

Wittig olefination

Enantioselective desymmetrization of prochiral ketones via an organocatalytic deprotonation process pp 764–768

Aurélie Claraz, Sylvain Oudeyer*, Vincent Levacher*

O

R

OTMS

RN

N

OHBn

OMeCat.Cat. (5 mol%)

BSA (1.5 equiv)THF, -78°C

OAr

Ar = 4-MeOC6H4R = alkyl, aryl... yield: 68-84%

ee up to 34%

(S)

+ first organocatalytic process for the transformation into silyl enolates+ low amount of catalyst required (as low as 2 mol%)+ BSA act as Brønsted base precursor and TMS provider

enantioselectivedesymmetrization

v

p-Stacking interactions at the service of [Cu]-bis(oxazoline) recycling pp 769–775

Dorian Didier, Emmanuelle Schulz*

O

N N

O

Cu(OTf)2

O

O

OEt

+

OH

O

OEt

7 efficient reuses

N-Pyrrolidine-2-ylmethyl)-2-hydroxy-3-aminopinanes as novel organocatalysts for asymmetric conjugate additions ofketones to a-nitroalkenes

pp 776–779

Dmitry E. Siyutkin, Alexander S. Kucherenko, Larisa L. Frolova, Alexander V. Kuchin, Sergei G. Zlotin*

R1 R2

O

R3

+catalyst (10 mol.%)

THF, RTR1 R2

O R3

R1,R2: H,H; -(CH2)3-, -CH2XCH2- (X = O, S)R3: Ph, 4-Cl-C6H4, 4-MeO-C6H4, 2-NO2-C6H4, 2,4-Cl2-C6H3, 2-thienyl

NH HN

Me

MeHO

Meyield up to 96%dr (syn/anti) up to 97/3ee (syn) up to 88%

catalyst

NO2

O2N

OTHER CONTENTS

Stereochemistry abstracts pp A165–A183

Cumulative author index pp I–III

*Corresponding author

Available online at www.sciencedirect.com

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 SciVerse Scopus®. Full text availableon SciVerse ScienceDirect®

ISSN 0957-4166

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