The use of polymer-bound triphenylphosphine in the stereochemical inversion of secondary alcohols

Comb Chem High Throughput Screen. 2000 Apr;3(2):103-6. doi: 10.2174/1386207003331706.

Abstract

Polymer-bound triphenylphosphine can replace triphenylphosphine in the Mitsunobu reaction to generate stereochemically inverted secondary alcohols. This method is comparable with the standard Mitsunobu reaction in terms of inversion of stereochemistry, yield, and reaction time, even for sterically very hindered secondary alcohols. The special merit of this reaction is that the excess polymer-bound triphenylphosphine and its by-products are easily removed by filtration from the reaction products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Molecular Structure
  • Organophosphorus Compounds / chemistry*
  • Polymers / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Organophosphorus Compounds
  • Polymers
  • triphenylphosphine