Organocascade Reactions of Enones Catalyzed by a Chiral Primary Amine

被引：180

作者：

Wu, Li-Yuan ^{[1
]}

Bencivenni, Giorgio ^{[1
]}

Mancinelli, Michele ^{[1
]}

Mazzanti, Andrea ^{[1
]}

Bartoli, Giuseppe ^{[1
]}

Melchiorre, Paolo ^{[1
]}

机构：

[1] Alma Mater Studiorum Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 39期

关键词：

asymmetric catalysis; domino reactions; ketones; organocatalysis; quaternary stereocenters; DIELS-ALDER REACTIONS; ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE CONSTRUCTION; CONJUGATE ADDITION; ACTIVATION; STRATEGIES; CHEMISTRY; ADVENT;

D O I：

10.1002/anie.200903280

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Primary amines do it differently: Acyclic α, β -unsaturated ketones are activated toward a characteristic stepwise double-Michael addition sequence by chiral primary amine catalysis, which offers a powerful alternative in the design of synthetically useful organocascade reactions (see scheme, EWG=electron-withdrawing group). This method complements the Diels-Alder reaction for the one-step synthesis of complex cyclohexane scaffolds with excellent optical purity. © 2009 Wiley-VCH Verlag GmbH & Co. KCaA.

引用

页码：7196 / 7199

页数：4

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