4.8 Article

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

Journal

ACS CATALYSIS
Volume 9, Issue 3, Pages 2286-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b04789

Keywords

Cu catalysis; atropisomer; C-N axial chirality; asymmetric catalysis; amides

Funding

  1. NSFC [21622206, 21871241]
  2. 973 project from the MOST of China [2015CB856600]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  4. Fundamental Research Funds for the Central Universities [WK2060190086]

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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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