Chiral squaramide as multiple H-bond donor organocatalysts for the asymmetric Michael addition of 1,3-dicarbonyl compounds to nitroolefins

被引：34

作者：

Dong, Ze ^{[1
]}

Qiu, Guofu ^{[1
]}

Zhou, Hai-Bing ^{[1
]}

Dong, Chune ^{[1
]}

机构：

[1] Wuhan Univ, Sch Pharmaceut Sci, State Key Lab Virol,Minist Educ, Lab Combinatorial Biosynth & Drug Discovery, Wuhan 430071, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 22-23期

关键词：

MANNICH REACTIONS; BIFUNCTIONAL ORGANOCATALYSIS; CINCHONINE-SQUARAMIDE; STRECKER REACTION; THIOUREA; QUATERNARY; CATALYSTS; EFFICIENT; NITROALKANES; CONSTRUCTION;

D O I：

10.1016/j.tetasy.2012.10.016

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of chiral bifunctional squaramide multiple H-bond donor organocatalysts have been designed and synthesized by the rational assembly of chiral privileged scaffolds of indanol and cinchona alkaloids. In the presence of 1 mol % 1a, the asymmetric Michael addition reaction of 1,3-dicarbonyl compounds to nitroolefins proceeded to provide the product in high yields (up to 92%) and with good to high ee values (up to 96%). The additional H-bond in this squaramide system plays a crucial role in enhancing the enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1550 / 1556

页数：7

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