Uses
Precursor to 1,1-disubstituted 1-propenes; reacts with primary Grignard reagents to give 2-(methyldiphenylsilyl)-3-
alkanones, which in turn lead to regioselectively derived methyldiphenylsilyl enol ethers or to 3-alkanones; reagent for the
synthesis of α-methyl-α,β-unsaturated esters.
Preparation
whereas the direct silylation of the lithium
enolate of an ester normally results in the formation of a mixture
of the α-silyl ester and the corresponding silyl ketene acetal, the
reaction of lithium ester enolates with methyldiphenylchlorosilane gives exclusively the α-methyldiphenylsilyl ester. This
direct C-silylation is the best general route to α-silyl esters.
Precautions
Ethyl 2-(Methyldiphenylsilyl)propanoate and other α-silyl carbonyl compounds are hydrolyzed under acidic or basic conditions to give the parent desilylated ester.
