Palladium Catalyzed Ring-Opening of Diazabicylic Olefins with 4-Halo-1,3-Dicarbonyl Compounds: Accessing 3(2H)-Furanone-Appended Cyclopentenes

We have realized a Pd-catalyzed ring-opening of diazabicyclic olefins with 4-halo-1,3-dicarbonyl compounds. This reaction resulted in the formation 3(2H)-furanone-appended hydrazino cyclopentenes. The proceeds via π-allylpalladium intermediate which is attacked by active methylene species, and an intramolecular nucleophilic substitution moiety furnishes 3(2H)-furanone-substituted cyclopentene. could extend this methodology to cyclopropane-appended spirotricyclic olefin for synthesizing spiro[2.4]hept-5-ene.