Highly Regioselective Silylation of α,β-Dihydroxyphosphonates: An Application to Stereoselective Synthesis of α-Amino-β-hydroxyphosphonic Acid Derivatives

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Abstract
tert-Butyldimethylsilylation of threo-α,β-dihydroxyphosphonates 1 and 6a,c-e proceeded with high degree of regioselectivity to give the corresponding β-siloxy derivatives. As an application of these findings, a stereocontrolled synthesis of erythro-α-amino-β-siloxyphosphonate 9 was achieved in an optically active form from α,β-dihydroxyphosphonate 1.

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