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

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.