Electrophilic Bromolactonization of Cyclopropyl Diesters Using Lewis Basic Chalcogenide Catalysts

Abstract

Abstract An efficient and regioselective electrophilic bromolactonization of cyclopropylmethyl diesters using triphenylphosphine sulfide (Ph 3 PS) or diphenyl selenide (Ph 2 Se) as the Lewis basic chalcogenide catalyst has been developed. It was observed that Ph 3 PS favored the formation of anti ‐diastereomer and yielded the multi‐functional γ‐lactones. Interestingly, the diastereoselectivity was reversed when using Ph 2 Se as a catalyst where the syn ‐product instead of the anti ‐product was favored. magnified image