Stereospecific coupling of H-phosphinates and secondary phosphine oxides with amines and alcohols: a general method for the preparation of optically active organophosphorus acid derivatives

J Org Chem. 2010 Jun 4;75(11):3890-2. doi: 10.1021/jo100473s.

Abstract

The reaction of H-phosphinates and secondary phosphine oxides with amines and alcohols proceeds highly stereospecifically to give the corresponding coupling products with inversion of configuration at the phosphorus center under the Atherton-Todd reaction conditions. This finding leads to the establishment of a general and efficient method for the synthesis of a variety of optically active organophosphorus acid derivatives from the easily available chiral H-phosphinates and secondary phosphine oxides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Amines / chemistry
  • Methods
  • Optical Rotation
  • Organophosphorus Compounds / chemical synthesis*
  • Oxides / chemistry
  • Phosphines / chemistry
  • Phosphorous Acids / chemistry
  • Stereoisomerism

Substances

  • Alcohols
  • Amines
  • Organophosphorus Compounds
  • Oxides
  • Phosphines
  • Phosphorous Acids
  • phosphine
  • metaphosphoric acid