anti-Selective Asymmetric Michael Reactions of Aldehydes and Nitroolefins Catalyzed by a Primary Amine/Thiourea

被引：93

作者：

Uehara, Hisatoshi ^{[1
,2
]}

Barbas, Carlos F., III ^{[1
,2
]}

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, Dept Mol Biol, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 52期

关键词：

aldehydes; amines; asymmetric synthesis; Michael addition; organocatalysis; MANNICH-TYPE REACTIONS; SYN-ALDOL REACTIONS; ENANTIOSELECTIVE CONJUGATE ADDITION; CHIRAL AMINO SULFONAMIDE; 3-PYRROLIDINECARBOXYLIC ACID; GENERAL ORGANOCATALYST; KETONES; EFFICIENT; DERIVATIVES; PYRROLIDINE;

D O I：

10.1002/anie.200905313

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(figure represented) It's finally here: Highly anti-selective Michael reactions of a functionalized aldehyde with nitroolefins have been realized using a primary amine/thiourea catalyst (see scheme; TBS = tert- butyldimethylsilyl). The reaction relies on a conformational strategy based on directing the formation of a Z-configured enamine intermediate. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

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收藏

页码：9848 / 9852

页数：5

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