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

De Run Li, Anyu He, J R Falck

Research output: Contribution to journalArticle

38 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)1756-1759
Number of pages4
JournalOrganic Letters
Volume12
Issue number8
DOIs
StatePublished - Apr 16 2010

Fingerprint

Thiourea
thioureas
Ketones
ketones
Amines
amines
catalysts
Catalysts
Boranes
boranes
Complexation
Hydrides
hydrides
induction
alcohols
Air
Alcohols
air

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts. / Li, De Run; He, Anyu; Falck, J R.

In: Organic Letters, Vol. 12, No. 8, 16.04.2010, p. 1756-1759.

Research output: Contribution to journalArticle

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