Asymmetric Michael Addition of α-Substituted Isocyanoacetates with Maleimides Catalyzed by Chiral Tertiary Amine Thiourea

被引：85

作者：

Bai, Jian-Fei ^{[1
,2
]}

Wang, Liang-Liang ^{[1
,2
]}

Peng, Lin ^{[1
]}

Guo, Yun-Long ^{[1
,2
]}

Jia, Li-Na ^{[1
,2
]}

Tian, Fang ^{[1
]}

He, Guang-Yun ^{[1
]}

Xu, Xiao-Ying ^{[1
]}

Wang, Li-Xin ^{[1
]}

机构：

[1] Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 06期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE CONJUGATE ADDITION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; ORGANOCATALYTIC CYCLIZATION; ISOCYANOESTERS; CYANOACETATES; CONSTRUCTION; DERIVATIVES; OXINDOLES;

D O I：

10.1021/jo2025288

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly diastereoselective and enantioselective Michael addition of alpha-substituted isocyanoacetates with maleimides catalyzed by bifunctional tertiary amine thioureas has been developed. Various chiral succinimide derivatives bearing adjacent quaternary and tertiary stereocenters were prepared in excellent yields (up to 98%), diastereoselectivities (up to 99:1), and enantioselectivities (up to 98% ee). The synthetic utility of chiral succinimide derivatives is also demonstrated in the preparation of h5-HT1d receptor agonist motifs.

引用

页码：2947 / 2953

页数：7

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