The reactions of a variety of ester and lactone enolates with methyldiphenylchlorosilane were studied. The C-versus 0-silylation, leading to the a-silyl ester or lactone and silyl ketene acetal, respectively, was studied as a function of the structure of the ester or lactone and the reaction conditions. It was found that all simple acetates are C-silylated irrespective of the steric demands of the alcohol portion of the ester. Esters that are monosubstituted in ...