Convergent synthesis of conjugated 1,2-disubstituted E-allylic alcohols from two aldehydes and methylenetriphenylphosphorane

Org Biomol Chem. 2012 Oct 21;10(39):7949-51. doi: 10.1039/c2ob26346g. Epub 2012 Aug 30.


β-Lithiooxyphosphonium ylides, made in situ from an aldehyde and methylenetriphenylphosphorane, react with a second aldehyde to form E-allylic alcohols. α-Branching and α,β-unsaturation in the second aldehyde, together with the lack of further substitution on the phosphorane carbon play important roles in selectivity. A range of these aldehydes, in addition to aromatic aldehydes as the second aldehyde also provided synthetically useful access to E-allylic alcohols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Molecular Structure
  • Organophosphorus Compounds / chemistry*
  • Propanols / chemical synthesis*
  • Propanols / chemistry
  • Stereoisomerism


  • Aldehydes
  • Organophosphorus Compounds
  • Propanols
  • allyl alcohol