Journal of organometallic chemistry

Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes

A Fu, G Kollegger, H Weidmann

Index: Fuerstner, Alois; Kollegger, Gerlinde; Weidmann, Hans Journal of Organometallic Chemistry, 1991 , vol. 414, # 3 p. 295 - 305

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Citation Number: 28

Abstract

Abstract Trimethylsilylmethyl ketones, readily from acyl chlorides, undergo a Reformatsky— Peterson reaction sequence to give 3-alkenoates regioselectivity. Acylsilanes, however, react with either zinc ester enolates or trimethylsilymethylmagnesium chloride to give the corresponding tertiary alcohols which, depending on their structure, spontaneously undergo either elimination or a Brook rearrangement—Peterson olefination sequence. These ...