Acetoxymaleic Anhydride as Ketene Equivalent in the Diels-Alder Reaction

Abstract

Acetoxymaleic anhydride (AMA) has been shown to be a versatile ketene equivalent in the Diels-Alder reaction for the conversion of 1,3-dienes into cyclohexanones. The new transformation has been applied to an alternate synthesis of methyl cis-dihydrojasmonate, an important jasmine fragrance, and to several model systems.