Reactions of β-trimethylstannylcyclohexanones with peracids: investigations into the stannyl-directed Baeyer–Villiger reaction

Abstract

The trimethylstannyl substituent raises the migratory aptitude of a primary β-carbon to be above that of a not otherwise activated secondary or tertiary carbon. This is apparent from the exclusive formation of the alkene acids 9–11 from Baeyer–Villiger reaction of the β-stannyl cyclohexanones 3–5. The stereoelectronic requirements of the stannyl-directed Baeyer–Villiger reaction were investigated using the axial β-trimethylstannylcyclohexanone 20.

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