Ketones, reaction with silane carbanions

Owing to the interest of optically active C-centered organosilanes, Paquette and co-workers (refs. 116-118) have applied the Haller-Bauer reaction to optically active non-enolizable a-silyl phenyl ketones. An optically active silane (Fig. 23) was obtained with retention of configuration (96 to 98 %). These results are interpreted on the basis of an initial a-silyl carbanion formation within a solvent shell that also encases benzamide. 

There is a silicon version of the Wittig reaction, known as the Peterson reac-tion. Reaction of an aldehyde or ketone with an a-silyl carbanion forms a -hydroxy silane, from which elimination of trialkylsilanol, RsSiOH, provides... 

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