Catalytic enantioselective allylic amination of unactivated terminal olefins via an ene reaction/[2,3]-rearrangement

J Am Chem Soc. 2012 Nov 14;134(45):18495-8. doi: 10.1021/ja307851b. Epub 2012 Oct 29.

Abstract

The enantioselective allylic amination of unactivated terminal olefins represents a direct and attractive strategy for the synthesis of enantioenriched amines. We have developed the first use of a nitrogen-containing reagent and a chiral palladium catalyst to convert unfunctionalized olefins into enantioenriched allylic amines via an ene reaction/[2,3]-rearrangement.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Allyl Compounds / chemistry*
  • Amination
  • Amines / chemical synthesis*
  • Amines / chemistry
  • Catalysis
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Allyl Compounds
  • Amines
  • Organometallic Compounds
  • Palladium