Enantioselective Atropisomeric Anilides Synthesis via Cu-Catalyzed Intramolecular Adjacent C-N Coupling

Catalytically asymmetric synthesis of atropisomeric compounds is an important research area in organic synthesis. However, in comparison with C-C atropisomers, the atropisomers caused by the restricted rotation of C-N single bonds have been given less attention because of the limited methods for accessing these compounds. Herein we report a Cu-catalyzed enantioselective intramolecular Ullmann-type amination reaction for the synthesis of C-N atropisomers. The C-N axial chirality was induced highly efficiently by the intramolecular adjacent C-N cross-coupling. The readily prepared N,N'-(cyclohexane-1,2-diyl)dipicolinamides showed high efficacy and stereoinduction (up to 99% ee).