Di(1R,2S,5R)-menthyl 2-Hydroxy-3-chloropropylphosphonate as a Useful Chiral Synthon for the Preparation of Enantiomerically Pure Phosphonic Acids

Abstract Stereochemically pure di(1R,2S,5R)-menthyl (S)- and (R)-2-hydroxy-3-chloropropylphosphonates were synthesized by reaction of di(1R,2S,5R)-menthyl ketophosphonate with chiral complexes prepared from sodium borohydride and (R,R)-(+)-tartaric acid or with (S,S)-(-)-tartaric acid. Dimenthyl 2-hydroxy-3-chloropropylphosphonate was utilized as a chiron for the preparation of biologically active products.