Synthesis 2015; 47(18): 2844-2850
DOI: 10.1055/s-0034-1380921
paper
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Formation of Cyano-Bearing All-Carbon Quaternary Stereocenters: Copper-Catalyzed N-Arylation via Kinetic Resolution­

Authors

  • Yan Long

    a   National & Local Joint Engineering Laboratory for New Petrochemical Materials and Fine Utilization of Resources, Hunan Normal University, No. 36 Lushan Road, Changsha 410081, P. R. of China   eMail: youlinzengcn@gmail.com
    b   Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou 510530, P. R. of China   eMail: cai_qian@gibh.ac.cn
  • Jialing Shi

    a   National & Local Joint Engineering Laboratory for New Petrochemical Materials and Fine Utilization of Resources, Hunan Normal University, No. 36 Lushan Road, Changsha 410081, P. R. of China   eMail: youlinzengcn@gmail.com
    b   Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou 510530, P. R. of China   eMail: cai_qian@gibh.ac.cn
  • Haoqiang Liang

    b   Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou 510530, P. R. of China   eMail: cai_qian@gibh.ac.cn
  • Youlin Zeng*

    a   National & Local Joint Engineering Laboratory for New Petrochemical Materials and Fine Utilization of Resources, Hunan Normal University, No. 36 Lushan Road, Changsha 410081, P. R. of China   eMail: youlinzengcn@gmail.com
  • Qian Cai*

    b   Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou 510530, P. R. of China   eMail: cai_qian@gibh.ac.cn
Weitere Informationen

Publikationsverlauf

Received: 23. März 2015

Accepted after revision: 30. April 2015

Publikationsdatum:
29. Juni 2015 (online)


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Abstract

A copper-catalyzed enantioselective N-arylation for the formation of cyano-bearing all-carbon quaternary stereocenters was developed via kinetic resolution of racemic 3-amino-2-(2-iodobenzyl)propanenitriles. The reaction afforded the desired coupling products in moderate enantioselectivity under catalysis by CuI and a BINOL-derived ligand.

Supporting Information