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Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts.
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ABSTRACT:
SUBMITTER: Li de R
PROVIDER: S-EPMC2860298 | biostudies-literature | 2010 Apr
REPOSITORIES: biostudies-literature
Publications
Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts.
Organic letters 20100401 8
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. ...[more]