An unexpected tandem enantioselective Michael addition/oxa-nucleophilic rearrangement reaction of β,γ-unsaturated α-keto esters catalyzed by cinchona alkaloids

被引：18

作者：

Wang, Hai-Feng ^{[1
]}

Zheng, Chang-Wu ^{[1
]}

Yang, Ying-Quan ^{[2
]}

Chai, Zhuo ^{[1
]}

Zhao, Gang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Synthet Organ Chem, Shanghai 200032, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 22期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetasy.2008.11.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Cinchona alkaloids were found to catalyze an enantioselective Michael addition/oxa-nucleophilic rearrangement reaction of beta,gamma-unsaturated alpha-keto esters 1 and malonates 2. Using the optimum catalyst quinine 4a, a series of the rearranged products 3 were obtained with up to 98% yield and 82% ee under mild reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2608 / 2615

页数：8

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