The chemistry of. alpha.-silyl carbonyl compounds. 12. A synthesis of 4-oxo carboxylic acids, 4-oxo aldehydes, and 1, 4-diketones from. gamma.-lactones

RM Betancourt de Perez, LM Fuentes…

Index: Betancourt de Perez, Rosa M.; Fuentes, Lelia M.; Larson, Gerald L.; Barnes, Charles L.; Heeg, Mary Jane Journal of Organic Chemistry, 1986 , vol. 51, # 11 p. 2039 - 2043

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Citation Number: 10

Abstract

The a-methyldiphenylsilyl derivatives of y-butyrolactone, y-valerolactone, and the cis lactone of 2-hydroxycyclohexaneacetic acid have been reacted with Grignard reagents. The a- silylated lactones of y-butyrolactone and y-valerolactone react with a single equivalent of Grignard reagent to give a 2-substituted 45-dihydrofuran, which can be hydrolyzed and oxidized to 4-oxo carboxylic acids, l, 4-diketones7 or 4-oxo aldehydes. The a-silylated ...