The chemistry of. alpha.-silyl carbonyl compounds. 17. Methyldiphenylsilylation of ester and lactone enolates

…, V Cruz de Maldonado, LM Fuentes…

Index: Larson, Gerald L.; Maldonado, Veronica Cruz de; Fuentes, Lelia M.; Torres, Luz E. Journal of Organic Chemistry, 1988 , vol. 53, # 3 p. 633 - 639

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Citation Number: 39

Abstract

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 ...