Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

Article abstract of DOI:10.1016/S0040-4020(97)10341-6

Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD- mix-α or -β reagent was examined to give a series of optically active threo-α,β-dihydroxyphosphonates. Good enantioselectivity (>88% ee) was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carded out with dimethyl phosphonate instead of diethyl phosphonate.