Bifunctional Organocatalytic Strategy for Inverse-Electron-Demand Diels-Alder Reactions: Highly Efficient In Situ Substrate Generation and Activation to Construct Azaspirocyclic Skeletons

被引：80

作者：

Jiang, Xianxing ^{[1
]}

Shi, Xiaomei ^{[1
]}

Wang, Shoulei ^{[1
]}

Sun, Tao ^{[1
]}

Cao, Yiming ^{[1
]}

Wang, Rui ^{[1
]}

机构：

[1] Lanzhou Univ, Sch Basic Med Sci, Inst Biochem & Mol Biol, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 09期

基金：

中国国家自然科学基金;

关键词：

asymmetric synthesis; cycloadditions; heterocycles; organocatalysis; synthetic methods; NITRO-MICHAEL ADDITION; ENANTIOSELECTIVE SYNTHESIS; CATALYSIS; KETONES; THIOUREAS; AMINE; ACID;

D O I：

10.1002/anie.201107716

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Skeletons in the flask: The first highly enantioselective organocatalytic version of the title reaction using an in-situ substrate generation/activation catalytic mode is described (see scheme). The reaction provides an efficient enantioselective construction of functionalized azaspirocyclic skeletons. The in-situ generation of the enolate provides a new way in which to use this important nucleophile in organic synthesis. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2084 / 2087

页数：4

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