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
收藏
页码：1756 / 1759
页数：4
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