IBiox[(-)-menthyl]: a sterically demanding chiral NHC ligand

The preparation and structural characterization of an exceedingly sterically demanding, rigid, and chiral NHC ligand, IBiox[(-)-menthyl], is described. The ability to use aryl chloride substrates in intramolecular palladium-catalyzed [alpha]-arylations has disclosed its unique reactivity and [C.sub.2]-symmetric IBiox[(-)-menthyl] has allowed the highly enantioselective formation of oxindoles with up to 99% ee.