Modular Bifunctional Chiral Thioureas as Versatile Organocatalysts for Highly Enantioselective Aza-Henry Reaction and Michael Addition

被引：37

作者：

Li, Hua ^{[1
]}

Zhang, Xu ^{[1
]}

Shi, Xin ^{[1
]}

Ji, Nan ^{[1
]}

He, Wei ^{[1
]}

Zhang, Shengyong ^{[1
]}

Zhang, Bangle ^{[2
]}

机构：

[1] Fourth Mil Med Univ, Sch Pharm, Dept Chem, Xian 710032, Peoples R China

[2] Fourth Mil Med Univ, Sch Pharm, Dept Pharmaceut, Xian 710032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 11-12期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; aza-Henry reaction; C-C bond formation; Michael addition; organic catalysis; NITRO-MANNICH REACTION; HETERO-DIELS-ALDER; TERTIARY STEREOCENTERS; ASYMMETRIC CATALYSIS; CINCHONA ALKALOIDS; NITROOLEFINS; ALDOL; CONSTRUCTION; ACTIVATION; QUATERNARY;

D O I：

10.1002/adsc.201200144

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A series of new modular bifunctional chiral thiourea organocatalysts were synthesized from natural Cinchona alkaloids and amino acids, and their performance in the aza-Henry reaction of nitroalkanes to imines, the Michael addition of acetylacetone to nitroolefins and the Michael addition of acetone to nitroolefins was investigated. Under the mild conditions, the important building blocks beta-nitro amines and gamma-nitro carbonyl compounds could be obtained in good yields (up to 95%) with excellent enantioselectivities (up to 99% ee) and diastereoselectivity (up to 17:1).

引用

页码：2264 / 2274

页数：11

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