Phosphine-mediated olefination between aldehydes and allenes: an efficient synthesis of trisubstituted 1,3-dienes with high E-selectivity

Org Lett. 2009 Aug 6;11(15):3498-501. doi: 10.1021/ol901334c.

Abstract

The phosphine-mediated olefination of aldehydes with electron-deficient allenes to afford trisubstituted conjugated dienes in fair to excellent yields with high E-selectivity is described. The reaction represents a new reactivity pattern of allenes with aldehydes and also provides a highly stereoselective synthetic method for preparing conjugated dienes. In the reaction, the phosphine acts as a nucleophilic promoter to generate in situ an active phosphorus ylide which mediates the intermolecular olefination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkadienes / chemistry*
  • Alkenes / chemistry*
  • Biological Products / chemistry*
  • Phosphines / chemistry*

Substances

  • Aldehydes
  • Alkadienes
  • Alkenes
  • Biological Products
  • Phosphines
  • propadiene
  • phosphine