Stereochemistry and mechanisms of the reactions of acylsilanes with alkoxides

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Abstract
Using chiral NpPhMeSiCOMe it is shown that the 'cleavage' pathway for the reaction of alkoxides with acylsilanes involves nucleophilic attack at the carbonyl group, followed by subsequent rearrangements which result in optically active NpPhMeSiOR and aldehyde. The 'rearrangement' pathway involves stereospecific migrations of the naphthyl and phenyl groups from silicon to different faces of the adjacent carbonyl group, resulting in chiral naphthylethanol and phenylethanol of opposite absolute configurations.

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