Preparation of cyclobutenones and cyclopent-2-enones via epoxy sulfone cyclizations

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Abstract
Epoxysulfones of the type [Formula: see text] react with about 2 equiv. of CH3MgI in THF to give 3-phenylsulfonylcyclobutanols and 3-phenylsulfonylcyclopentanols in good to excellent yields. 3-Alkyl-3-phenylsulfonylcyclobutanols and -cyclopentanols can be obtained either from the appropriately substituted epoxides or by alkylation of the dianion of the parent 3-phenylsulfonylcycloalkanols. Oxidation of these alcohols with Jones' reagent followed by treatment of the crude ketones with triethylamine leads to 3-substituted cyclobutenones and cyclopent-2-enones.

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