Organocatalyzed highly stereoselective Michael addition of ketones to alkylidene malonates and nitroolefins using chiral primary-secondary diamine catalysts based on bispidine

被引：57

作者：

Liu, Jie ^{[1
]}

Yang, Zhigang ^{[1
]}

Liu, Xiaohua ^{[1
]}

Wang, Zhen ^{[1
]}

Liu, Yanling ^{[1
]}

Bai, Sha ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 19期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC ALDOL REACTIONS; ENANTIOSELECTIVE CONJUGATE ADDITION; 1,3-DICARBONYL COMPOUNDS; ALDEHYDES; AMINE; THIOUREA; STEREOCENTERS; 1,4-ADDITION; ENONES;

D O I：

10.1039/b910939k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organocatalysts containing primary-secondary diamines based on bispidine have been developed to catalyze the asymmetric Michael addition of ketones to alkylidene malonates and nitroalkenes. The corresponding products were obtained in high yields (up to 99%) with high diastereoselectivities (up to 99: 1) and high enantioselectivities (up to 97% ee) under mild conditions using either environmentally benign water as the solvent or no solvent.

引用

页码：4120 / 4127

页数：8

共 74 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].