The chemistry of. alpha.-silyl carbonyl compounds. 10. A two-step preparation of. alpha.-alkylidene. gamma.-lactones from. gamma.-lactones: a synthesis of (.+-.)- …

GL Larson, RM Betancourt de Perez

Index: Larson, Gerald L.; Perez, Rosa M. Betancourt de Journal of Organic Chemistry, 1985 , vol. 50, # 25 p. 5257 - 5260

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Citation Number: 28

Abstract

y-Butyrolactone, y-valerolactone, and the cis lactone of 2-hydroxycyclohexaneacetic acid have been C-silylated via their respective lithium enolates with diphenylmethylchlorosilane. The resulting a-silylated y-lactones can be deprotonated and condensed with aldehydes and ketones to give a-alkylidene y-lactones in moderate to excellent yield. The enolate of the a-diphenylmethylsilyl cis lactone of 2-hydroxycyclohexaneacetic acid condensed with ...