The Reaction of Cyclopropyl Ketones with Acetyl Methanesulfonate. An efficient ring opening under neutral conditions with regiospecific enol acetate formation and stereo-controlled nucleophilic addition. Preliminary communication

Cyclopropyl ketones are readily cleaved under neutral conditions at room temperature by the combined action of acetyl methanesulfonate and nucleophiles such as Br^?, I^?, and MsO^?. The high-yield reaction involves regiospecific enol acetate formation with a stereoselectivity of nucleophile addition which is compatible with an S_N2-type opening of the cyclopropyl ring.