Enantioselective, Organocatalytic Reduction of Ketones using Bifunctional Thiourea-Amine Catalysts

被引：40

作者：

Li, De Run ^{[1
]}

He, Anyu ^{[1
]}

Falck, J. R. ^{[1
]}

机构：

[1] Univ Texas SW Med Ctr Dallas, Dept Biochem & Pharmacol, Dallas, TX 75390 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 08期

关键词：

ASYMMETRIC REDUCTION; MECHANISM; ALCOHOLS;

D O I：

10.1021/ol100365c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Prochiral ketones are reduced to enantioenriched, secondary alcohols using catecholborane and a family of air-stable, bifunctional thiourea amine organocatalysts. Asymmetric induction is proposed to arise from the in situ complexation between the borane and chiral thiourea amine organocatalyst resulting in a stereochemically biased boronate amine complex. The hydride in the complex is endowed with enhanced nucleophilicity while the thiourea concomitantly embraces and activates the carbonyl.

引用

页码：1756 / 1759

页数：4