Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefins

被引：247

作者：

Wang, J ^{[1
]}

Li, H

Duan, WH

Zu, LS

Wang, W

机构：

[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA

[2] Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 21期

关键词：

D O I：

10.1021/ol0519137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel binaphthyl-derived amine thiourea organocatalyst has been developed and demonstrated to efficiently catalyze Michael addition reactions (using as low as 1 mol % loading) of diketones to nitroalkenes with remarkably high enantioselectivities.

引用

页码：4713 / 4716

页数：4

共 48 条

[1] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].

Alexakis, A ;

Benhaim, C ;

Rosse, S ;

Humam, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263

[2] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].

Andrey, O ;

Alexakis, A ;

Bernardinelli, G .

ORGANIC LETTERS, 2003, 5 (14) :2559-2561

[3] Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts [J].

Berkessel, A ;

Cleemann, F ;

Mukherjee, S ;

Müller, TN ;

Lex, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :807-811

[4] Second-generation organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones [J].

Berkessel, A ;

Mukherjee, S ;

Cleemann, F ;

Müller, TN ;

Lex, J .

CHEMICAL COMMUNICATIONS, 2005, (14) :1898-1900

[5]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[6] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Tanaka, F ;

Barbas, CF .

SYNTHESIS-STUTTGART, 2004, (09) :1509-1521

[7] Asymmetric catalysis .103. Enantioselective Michael addition of 1,3-dicarbonyl compounds to conjugated nitroalkenes [J].

Brunner, H ;

Kimel, B .

MONATSHEFTE FUR CHEMIE, 1996, 127 (10) :1063-1072

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

Christoffers, J ;

Baro, A .

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

[9] 5-Pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nitro-olefins [J].

Cobb, AJA ;

Longbottom, DA ;

Shaw, DM ;

Ley, SV .

CHEMICAL COMMUNICATIONS, 2004, (16) :1808-1809

[10] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].

Córdova, A ;

Watanabe, S ;

Tanaka, F ;

Notz, W ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867

← 1 2 3 4 5 →