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.