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

De Run Li; Anyu He; J R Falck

doi:10.1021/ol100365c

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

De Run Li, Anyu He, J R Falck

Biochemistry

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

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.

Original language	English (US)
Pages (from-to)	1756-1759
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	8
DOIs	https://doi.org/10.1021/ol100365c
State	Published - Apr 16 2010

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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AU - He, Anyu

AU - Falck, J R

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Y1 - 2010/4/16

N2 - 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.

AB - 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.

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

Abstract

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