Controllable Cycilization Reactions of 2-(2′,3′-Allenyl)acetylacetates Catalyzed by Gold and Palladium Affording Substituted Cyclopentene and 4,5-Dihydrofuran Derivatives with Distinct Selectivity

Efficient room-temperature syntheses of cyclopentenes and 4,5-dihydrofurans with different substitution patterns were performed starting from the same materials (i.e., 2-(2',3'-allenyl)acetyl acetates). Depending on the choice of metal catalyst, the Au-catalyzed reaction afforded C-attack-5-endo cyclization products 2, whereas the Pd-catalyzed one led to the formation of O-attack-5-exo cyclization products 3. The selectivity may be explained by the steric and electronic effects of the substrates and catalysts.