Highly enantioselective 1,4-addition of diethyl phosphite to enones using a dinuclear Zn catalyst

Chemistry. 2009;15(12):2738-41. doi: 10.1002/chem.200802688.

Abstract

Zinc benefits: The first catalytic asymmetric phospha-Michael addition of enones has been developed. Under mild reaction conditions, the gamma-oxo phosphonates could be obtained in high yields (up to 99%) with excellent enantioselectivities (93-99% ee; see scheme). The strategy makes the asymmetric synthesis of biologically important phosphonate compounds more accessible.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry
  • Phosphites / chemistry*
  • Phosphorylation
  • Stereoisomerism
  • Zinc / chemistry*

Substances

  • Ketones
  • Organophosphonates
  • Phosphites
  • Zinc