Scope and stereochemical course of the addition of (trimethylsilyl) allenes to ketones and aldehydes. A regiocontrolled synthesis of homopropargylic alcohols

…, DJ Carini, CA Kwasigroch

Index: Danheiser, Rick L.; Carini, David J.; Kwasigroch, Carrie A. Journal of Organic Chemistry, 1986 , vol. 51, # 20 p. 3870 - 3878

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Citation Number: 96

Abstract

The reaction of (trimethylsily1) allenes with aldehydes and ketones in the presence of titanium tetrachloride provides a regiocontrolled route to homopropargylic alcohols of a variety of substitution types. The addition of 1-alkyl-substituted (trimethylsily1) allenes to carbonyl compounds furnishes the desired acetylenes directly, while reactions involving allenylsilanes 6, 7, and 9 initially produce mixtures of acetylenes and (trimethylsily1) vinyl ...