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

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 resul...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 8; pp. 1756 - 1759
Main Authors Li, De Run, He, Anyu, Falck, J. R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.04.2010
Amer Chemical Soc
Subjects
Amines - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cross-Linking Reagents - chemistry
Ketones - chemistry
Oxidation-Reduction
Physical Sciences
Science & Technology
Stereoisomerism
Substrate Specificity
Thiourea - chemistry
ALCOHOLS
MECHANISM
ASYMMETRIC REDUCTION
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Summary: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.
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol100365c