The Rhodium‐Catalyzed Carbene Cyclization Cycloaddition Cascade Reaction of Vinylsulfonates

Abstract

AbstractVinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodium‐catalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8 and (+)‐15, were readily available from hydroxy esters, e.g. 1 and the cyclopenta‐1,3‐dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A ruthenium‐catalyzed asymmetric transfer hydrogenation was found to desymmetrize the meso‐cyclopenta‐1,3‐dione 12 efficiently.