Abstract

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 (4 S,5 S)-4-diethylphosphono-2,2-dimethyl-5-hydroxymethyl-1,3-dioxolane 6, a potentially useful chiron for asymmetric synthesis of α-heteroatom-substituted phosphonates.

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