A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan†
Abstract
A silver-catalyzed diastereoselective one-pot domino cyclization-migration/inverse electron-demand oxo-Diels–Alder reaction has been disclosed in this communication through the in situ generated cyclobutane-fused furan intermediate with 4-vinyl-2,3-dioxopyrrolidine for the construction of 2-oxopyrrolidine-fused tricyclic compounds in moderate to good yields with a broad substrate scope under mild conditions. This new synthetic protocol features good efficiency and atom- and step-economy. A plausible reaction mechanism has also been proposed on the basis of previous reports, NMR tracing and control experiments.