Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of vinylphosphonates. An application to the stereocontrolled synthesis of (4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

Article abstract of DOI:10.1016/0957-4166(95)00014-G

The asymmetric dihydroxylation (AD) reaction of vinylphosphonates with AD-mix-α and -β reagents was successfully applied to the enantioselective synthesis of threo-α,β-dihydroxyphosphonates. β-Aryl substituents on the vinyl phosphonates were found to be good directors for the reaction with respect to the yield and enantioselectivity. The utility of chiral α,β-dihydroxyphosphonate 2c was illustrated by the stereocontrolled synthesis of (4S,5S)-4-diethylphosphono-2,2-dimethyl-5-hydroxymethyl-1,3-dioxolane 6, a potentially useful chiron for asymmetric synthesis of α-heteroatom-substituted phosphonates.