Phase transfer catalyzed enantioselective Strecker reactions of alpha-amido sulfones with cyanohydrins

J Org Chem. 2006 Dec 22;71(26):9869-72. doi: 10.1021/jo061566u.

Abstract

A study into the use of a chiral phase-transfer catalyst in conjunction with acetone cyanohydrin to effect the enantioselective formation of alpha-amino nitriles from alpha-amido sulfones is described. This novel catalytic asymmetric Strecker reaction is analyzed with regard to the possible mechanistic basis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonates / chemistry
  • Catalysis
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Phase Transition
  • Potassium / chemistry
  • Stereoisomerism
  • Sulfones / chemistry*
  • Water / chemistry

Substances

  • Carbonates
  • Nitriles
  • Sulfones
  • cyanohydrin
  • Water
  • potassium carbonate
  • Potassium