A high-yielding preparation of homoallylic sulfones 2 entails the treatment of allylic tosylacetate esters 1 with stoichiometric or substoichiometric quantities of BSA and substoichiometric quantities of KOAc under conventional thermal or microwave conditions. A possible mechanism involves silyl ketene acetal formation, [3,3]-sigmatropic rearrangement, and desilylation-decarboxylation. BSA=N,O-bis(trimethylsilyl)acetamide; Ts=p-toluenesulfonyl.
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Bourgeois et al. (2004) studied this question.
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