Regio- and diastereoselective synthesis of functionalized hydroxyhexahydrocyclopenta[b]furancarboxylates by oxidative radical cyclization of cyclic β-keto esters with alkenes

摘要

Oxidative radical cyclization of cyclic β-keto esters with alkenes is described. Substituted hydroxyhexahydrocyclopenta[b]furancarboxylates having substituents at the 2-position were produced in a diastereoselective manner when the reactions were carried out in the presence of CAN and Cu(OAc)_2. As application of the reactions, syntheses of the keto sulfonamide and the cyclic hemiacetal containing an exo-olefinic moiety were accomplished by the use of the β-enamino ester and aryl-substituted allene, respectively.