Chiral phosphaalkene-oxazoline ligands for the palladium-catalyzed asymmetric allylic alkylation

Org Lett. 2010 Oct 15;12(20):4667-9. doi: 10.1021/ol1020652.

Abstract

Enantioselective catalysis in moderate to excellent yields and ee's has been accomplished using a phosphaalkene-based ligand system. Specifically, the palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate using a chiral P(sp(2)),N(sp(2)) ligand proceeds with a variety of malonate nucleophiles in 73-95% yield (79-92% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Alkylation
  • Allyl Compounds / chemistry*
  • Catalysis
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Oxazoles / chemistry*
  • Palladium / chemistry*
  • Phosphates / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Allyl Compounds
  • Ligands
  • Oxazoles
  • Phosphates
  • Palladium