Selective formation of alkenes from trimethylsilylmethyl ketones and from 
acylsilanes

Fürstner, Alois; Kollegger, Gerlinde; Weidmann, Hans

doi:10.1016/0022-328X(91)86327-M

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Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes

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Citation

Fürstner, A., Kollegger, G., & Weidmann, H. (1991). Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes. Journal of Organometallic Chemistry, 414(3), 295-305. doi:10.1016/0022-328X(91)86327-M.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000E-E68F-2

Abstract

Trimethylsilylmethyl ketones, readily available from acyl chlorides, undergo a Reformatsky-Peterson reaction sequence to give 3-alkenoates regioselectively. Acylsilanes, however, react with either zinc ester enolates or trimethylsilylmethylmagnesium chloride to give the correspondmg tertiary alcohols which, depending on their structure, spontaneously undergo either elimination or a Brook rearrangement-Peterson
olefination sequence. These reactions allow the selective formation of vinylsilanes.