Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts.

ABSTRACT: 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.

SUBMITTER: Li de R 

PROVIDER: S-EPMC2860298 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature