Chiral Amine Thiourea-Promoted Enantioselective Michael Addition Reactions of 3-Substituted Benzofuran-2(3H)-ones to Maleimides

被引：64
|
作者：
Li, Xin [1 ,2 ]
Hu, Shenshen [3 ]
Xi, Zhiguo [1 ,2 ]
Zhang, Long [3 ]
Luo, Sanzhong [3 ]
Cheng, Jin-Pei [1 ,2 ]
机构：
[1] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 24期
基金：
中国博士后科学基金;
关键词：
CATALYTIC ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; 1,3-DICARBONYL COMPOUNDS; QUATERNARY; OXINDOLES; ORGANOCATALYSIS; CONSTRUCTION; DAPHNODORIN; GUANIDINE;
D O I：
10.1021/jo101832e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly diastereo- and enantioselective Michael addition reaction with respect to prochiral 3-substituted benzofuran-2(3H)-ones and maleimides by a chiral bifunctional thiourea-tertiary amine catalyst was investigated. The corresponding adducts, containing a quaternary center at the C3-position of the benzofuran-2(3H)-one as well as a vicinal tertiary center, were generally obtained in high yields (up to 99%) with very good diastereo- (up to > 20:1 dr) and enantioselectivities (up to 97% cc).
引用
收藏
页码：8697 / 8700
页数：4
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