Organocatalytic Kinetic Resolution of Sulfoximines

J Am Chem Soc. 2016 Feb 24;138(7):2166-9. doi: 10.1021/jacs.6b00143. Epub 2016 Feb 10.

Abstract

An efficient kinetic resolution of sulfoximines with enals was realized using chiral N-heterocyclic carbene (NHC) catalysts. The stereoselective amidation proceeds without additional acyl transfer agent. Both enantiomers of the sulfoximines can be obtained with excellent ee values (up to 99% ee and -97% ee, respectively). Performing the catalysis on a gram scale allowed using the recovered sulfoximine (+)-1j in an asymmetric synthesis of FXa inhibitor F.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heterocyclic Compounds / chemistry*
  • Imines / chemical synthesis*
  • Imines / chemistry
  • Kinetics
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Heterocyclic Compounds
  • Imines
  • carbene
  • Methane