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
收藏
页码：2608 / 2615
页数：8
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