Vj. Blazis et al., ASYMMETRIC-SYNTHESIS OF ALPHA-HYDROXY-PHOSPHONAMIDES, PHOSPHONATES AND PHOSPHONIC-ACIDS, Tetrahedron : asymmetry, 5(4), 1994, pp. 499-502
The addition of the anion of the bicyclic chiral phosphorous acid diam
ide 1a to aldehydes in THF solution gave alpha-hydroxy phosphonamides
in good yield and good diastereoselectivity (54-93% de). The phosphona
mides were hydrolyzed with aqueous HCl in dioxane to give alpha-hydrox
y phosphonic acids. Methylation of the resulting phosphonic acids with
diazomethane gave alpha-hydroxy dimethyl phosphonates without loss of
stereochemical integrety.