Efficient method for the asymmetric reduction of α- and β-ketophosphonates

An efficient and versatile method for the asymmetric reduction of alpha- and beta- ketophosphonates using chiral reactant derived from sodium borohydride and L-(+)-or D-(-)- tartaric acid is developed. The methodology was used for the preparation of a number of biologically interesting enantiomerically pure products: including 2,3-epoxypropylphosphonate 11, 2-hydroxy-3-aminopropylphosphonic acid 14 ( phosphoGABOB), phospho-carnitine 19, and others in multigram scale. (c) 2007 Elsevier Ltd. All rights reserved.