From racemic alcohols to enantiopure amines: Ru-catalyzed diastereoselective amination

J Am Chem Soc. 2014 Sep 10;136(36):12548-51. doi: 10.1021/ja5058482. Epub 2014 Aug 29.

Abstract

A commercially available ruthenium(II) PNP-type pincer catalyst (Ru-Macho) promotes the formation of α-chiral tert-butanesulfinylamines from racemic secondary alcohols and Ellman's chiral tert-butanesulfinamide via a hydrogen borrowing strategy. The formation of α-chiral tert-butanesulfinylamines occurs in yields ranging from 31% to 89% with most examples giving >95:5 dr.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alcohols / chemistry*
  • Amination
  • Amines / chemical synthesis*
  • Amines / chemistry
  • Catalysis
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Amines
  • Organometallic Compounds
  • Ruthenium