Catalytic enantioselective conjugate additions with α,β-unsaturated sulfones

被引：51

作者：

Li, Hongming ^{[1
]}

Song, Jun ^{[1
]}

Deng, Li ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

TETRAHEDRON | 2009年 / 65卷 / 16期

关键词：

Organocatalyst; Hydrogen bonding; Cinchona alkaloids; Chiral sulfones; Conjugate addition; ASYMMETRIC MICHAEL ADDITION; QUATERNARY STEREOCENTERS; CINCHONA ALKALOIDS; VINYL SULFONES; CONSTRUCTION; ALDEHYDES; ALPHA; ACIDS; REDUCTION; REAGENTS;

D O I：

10.1016/j.tet.2008.11.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the development of a highly efficient catalytic asymmetric conjugate addition alpha,beta-unsaturated sulfones. Utilizing practical bifunctional organic catalysts and involving air- and moisture-tolerant conditions, conjugate additions of a wide range of Michael donors to alpha,beta-unsaturated sulfones proceeded in excellent enatioselectivity/diastereoselectivity and high yield. This efficient and operationally simple new catalytic asymmetric reaction should provide a versatile approach for the asymmetric synthesis of chiral sulfones bearing all-carbon quaternary stereocenters. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3139 / 3148

页数：10

共 33 条

[1]

Alonso DA, 2003, SYNTHESIS-STUTTGART, P277

[2] Catalytic asymmetric conjugate addition of grignard reagents to (α,β-unsaturated sulfones [J].

Bos, Pieter H. ;

Minnaard, Adriaan J. ;

Feringa, Ben L. .

ORGANIC LETTERS, 2008, 10 (19) :4219-4222

[3] Formation of quaternary stereocenters by copper-catalyzed Michael reactions with L-valine amides as auxiliaries [J].

Christoffers, J .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (20) :4862-4867

[4] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].

Christoffers, J ;

Baro, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690

[5]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

[6]

2-V

[7]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

[8]

2-V

[9] ASYMMETRIC MICHAEL ADDITION OF CHIRAL IMINES TO PHENYLVINYLSULFONE - PREPARATION OF KEY CHIRAL BUILDING-BLOCKS FOR THE SYNTHESIS OF ASPIDOSPERMA AND HUNTERIA ALKALOIDS [J].

DANGELO, J ;

REVIAL, G ;

COSTA, PRR ;

CASTRO, RN ;

ANTUNES, OAC .

TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :199-202

[10] Catalytic enantioselective addition of diorganozinc reagents to vinyl sulfones [J].

Desrosiers, Jean-Nicolas ;

Bechara, William S. ;

Charette, Andre B. .

ORGANIC LETTERS, 2008, 10 (11) :2315-2318

← 1 2 3 4 →