Gearing Effects on -9-Anth-PyBidine-Cu(OAc)-Catalyzed Asymmetric Direct Haloimidation Reactions of Alkylidenemalononitriles.

A newly developed -9-anthranylmethyl bis(imidazolidine)pyridine (-9-Anth-PyBidine)-Cu(OAc) complex catalyzed asymmetric haloimidation reactions of alkylidenemalononitriles with -bromosuccinimide and -chlorosuccinimide, employing the succinimide moiety directly as a copper-bound nucleophile. The anthranyl substituent showed a gearing effect that produced a well-organized asymmetric sphere involving the -H proton of the imidazolidine ring in the ligand. The gearing effect afforded hydrogen bonding-assisted copper-catalyzed haloimidation reactions with high enantioselectivity.