Dearomatizing Cyclization of 2-Iodoindoles by Oxidative NHC Catalysis to Access Spirocyclic Indolenines and Oxindoles Bearing an All Carbon Quaternary Stereocenter.

An intramolecular dearomatizing spirocyclization of indoles by oxidative N-heterocyclic carbene catalysis is reported. C2-iodinated indoles are used as substrates in combination with aroyl azolium ions as acceptors, which provides C2-iodinated indolenines containing an all carbon quaternary stereocenter. The products are readily further C2-functionalized and give access to valuable oxindoles by simple hydrolysis in very good overall yields and excellent enantioselectivities.