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

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
› Author Affiliations
Further Information

Publication History

Received: 23 March 2015

Accepted after revision: 30 April 2015

Publication Date:
29 June 2015 (online)


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