Catalytic intermolecular aldehyde-ketone coupling via acyl phosphonates

J Org Chem. 2009 Mar 6;74(5):2197-9. doi: 10.1021/jo8026627.

Abstract

The first catalytic intermolecular aldehyde-ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate-phosphate rearrangement. These anions readily react with activated ketones to form acyloin type coupling in 41-95% yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Ketones / chemistry*
  • Molecular Structure
  • Organophosphonates / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Ketones
  • Organophosphonates