New highly enantioselective thiourea-based bifunctional organocatalysts for nitro-Michael addition reactions

被引：99

作者：

Wei, Shengwei

Yalalov, Denis A.

Tsogoeva, Svetlana B.

Schmatz, Stefan

机构：

[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

[2] Univ Gottingen, Inst Phys Chem, D-37077 Gottingen, Germany

来源：

CATALYSIS TODAY | 2007年 / 121卷 / 1-2期

关键词：

asymmetric catalysis; Michael addition; bifunctional organocatalysts; DFT calculations; transition states;

D O I：

10.1016/j.cattod.2006.11.018

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new and effective organocatalytic system, primary amine derived chiral thiourea catalyst and AcOH/H2O additive, which converts different ketones to gamma-nitroketones in high yields (82-99%) and enantioselectivities (90-99%) is described. The transition state geometries for formation of R and S enantiomers in this Michael addition have been calculated and analyzed. It is shown that only one oxygen atom of the nitro group is bound to the thiourea moiety, in juxtaposition to the literature-known working hypothesis which involves a bonding of both oxygens. (c) 2006 Elsevier B.V. All rights reserved.

引用

页码：151 / 157

页数：7

共 57 条

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