Enantioselective Dearomative Mizoroki–Heck Reaction of Naphthalenes

A palladium-catalyzed intramolecular enantioselective Mizoroki–Heck reaction of naphthalenes has been developed via dearomative migratory insertion of an endocyclic π-bond of naphthalene, followed by δ-hydride elimination. This reaction relies on the use of chiral sulfonamide phosphine type Xu-Phos ligand, which successfully inhibits the competitive and undesired C–H arylation reaction and efficiently promotes the formation of spirooxindole and spiroisoindolin-1-one products. Synthetic transformations of the product afford a series of unique heterocyclic compounds with enantiomeric excess (ee) values retained.