Enantioselective Atropisomeric Anilides Synthesis via Cu-Catalyzed Intramolecular Adjacent C–N Coupling
ACS Catalysis2019Vol. 9(3), pp. 2286–2291
Citations Over TimeTop 10% of 2019 papers
Abstract
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).
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