Chiral Iodine-Catalyzed Dearomatizative Spirocyclization for the Enantioselective Construction of an All-Carbon Stereogenic Center.

The first enantioselective dearomatizative spirocyclization of 1-hydroxy-N-aryl-2-naphthamide derivatives has been accomplished by chiral organoiodine catalysis to stereoselectively create an all-carbon stereogenic center, providing a straightforward approach to access spirooxindole derivatives in good yields and with high to excellent levels of enantioselectivity. Chiral hypervalent phenyl-λ(3) -iodanes generated in situ from the oxidation of the chiral phenyl iodine actually participate in the asymmetric oxidative dearomatizative spirocyclization reaction.