Copper-Catalyzed Desymmetric Intramolecular Ullmann C–N Coupling: An Enantioselective Preparation of Indolines

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Abstract

The first highly enantioselective copper-catalyzed intramolecular Ullmann C-N coupling reaction has been developed. The asymmetric desymmetrization of 1,3-bis(2-iodoaryl)propan-2-amines catalyzed by CuI/(R)-BINOL-derived ligands led to the enantioselective formation of indolines in high yields and excellent enantiomeric excesses. This method was also applied to the formation of 1,2,3,4-tetrahydroquinolines in high yields and excellent enantioselectivity.

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