Enantioselective strecker reaction of phosphinoyl ketoimines catalyzed by in situ prepared chiral N,N'-dioxides

J Org Chem. 2007 Jan 5;72(1):204-8. doi: 10.1021/jo062006y.

Abstract

The enantioselective Strecker reaction of N-diphenylphosphinoyl ketoimines has been achieved by use of in situ prepared chiral N,N'-dioxide catalyst from l-piperidinamide 3f and m-chloroperoxybenzoic acid (m-CPBA). Excellent yields (up to 99%) and high enantioselectivities (up to 92% ee) were obtained. In particular, in situ prepared catalyst with readily available chiral material made the procedure more convenient. Moreover, the l-piperidinamide 3f-derived N,N'-dioxide 9 could be recycled and reused at least five times without any loss of either catalytic activity or enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Imines / chemistry*
  • Molecular Structure
  • Oxides / chemistry*
  • Solvents
  • Stereoisomerism
  • Temperature

Substances

  • Imines
  • Oxides
  • Solvents