A new and efficient asymmetric synthesis of 1-amino-1-alkylphosphonic acids

Abstract

A new and efficient method for the asymmetric Synthesis of 1-amino-1-alkyl Phosphonic acids is described. It involves a diastereoselective alkylation of a bicyclic chloromethyl Phosphonamide derived from (S)-2-anilinomethylpyrrolidine, with subsequent conversions leading to an amino compound by the Staudinger method. Acid hydrolysis affords the target molecule of high enantiomeric purity and good yield. © 2000 John Wiley & Sons, Inc.