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

页码：8697 / 8700

页数：4

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