Rationally Designed Amide Donors for Organocatalytic Asymmetric Michael Reactions

被引：48

作者：

Tan, Bin ^{[1
,2
,3
]}

Hernandez-Torres, Gloria ^{[1
,2
,3
,4
]}

Barbas, Carlos F., III ^{[1
,2
,3
]}

机构：

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

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

[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

[4] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 22期

关键词：

amides; asymmetric synthesis; cinchona alkaloids; Michael addition; organocatalysis; ENANTIOSELECTIVE 1,4-ADDITION REACTIONS; C BOND FORMATION; CONJUGATE ADDITION; HIGHLY EFFICIENT; HENRY REACTION; CINCHONA ALKALOIDS; PROTECTED; 2-AMINO-1-NITROETHENES; MULTISUBSTITUTED CYCLOPENTANES; BIFUNCTIONAL ORGANOCATALYSTS; TRIFLUOROETHYL THIOESTERS;

D O I：

10.1002/anie.201200996

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Amide nucleophiles on demand: Rationally designed pyrazoleamides function as Michael donors in urea-catalyzed asymmetric Michael reactions with excellent chemical and optical yields (see scheme). The pyrazoleamide group performs as an ester equivalent, a directing group, an activating group, and functions as a good leaving group in further transformations of the product. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5381 / 5385

页数：5

共 93 条

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