Journal of Organic Chemistry p. 5260 - 5267 (1985)
Update date:2022-08-04
Topics:
Larson, Gerald L.
Hernandez, David
Lopez-Cepero, Ingrid Montes de
Torres, Luz E.
A variety of α-diphenylmethylsilyl esters have been prepared and reacted with Grignard reagents.The reaction is relatively slow in refluxing THF and can be controlled to allow the addition of 1 equiv of the Grignard reagent, providing the corresponding β-keto silane.Protiodesilylation of the β-keto silane results in the overall conversion of an ester to a ketone.This ester to ketone methodology has been applied to a two-step synthesis of the pheromone of the Douglas fir tussock moth.The β-keto silanes are viable precursors to regioselectively generated enol silyl ethers.The reaction of ethyl 2-methyl-2-(diphenylmethylsilyl)propionate with vinylmagnesium bromide or 2-methyl 1-propenylmagnesium bromide results in the addition of 2 equiv of the Grignard reagent, the second in a Michael fashion.
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(1982)Doi:10.1039/c39850000961
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(1985)Doi:10.1016/0031-9422(88)83045-0
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(1986)