Palladium-catalyzed reactions of alkenyloxiranes with carbon monoxide

Reaction of alkenyloxiranes with carbon monoxide in the presence of palladium catalyst gives unsaturated esters, β-lactones, dienes, and allylic alcohols. The selectivity of the reaction depends on the nature of the alkenyloxiranes. Carbonylation pruducts were obtained in the reaction of terminal alkenyloxiranes and alkenyloxirans having electron-donating substituent, whereas carbonylation scarcely took place in the reaction of alkenyloxiranes having electron-withdrawing groups; dienes and allylic alcohols were produced instead of carbonylation products.