Synthesis 2020; 52(10): 1498-1511
DOI: 10.1055/s-0037-1610749
paper
© Georg Thieme Verlag Stuttgart · New York

Highly Enantioselective Rh-Catalyzed Arylation of N,N-Dimethylsulfamoyl-Protected Aldimines and Cyclic N-Sulfonylimines with Chiral Phenyl Backbone Sulfoxide-Olefin Ligands

Feng Xue
a   College of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453002, P. R. of China   Email: fxuehist@sina.com
,
Qibin Liu
b   Dalian Allychem Co., Ltd, 5 Jinbin Road, Dalian 116620, P. R. of China   Email: qliu@allychem.com
,
Yong Zhu
a   College of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453002, P. R. of China   Email: fxuehist@sina.com
,
Yifei Huang
a   College of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453002, P. R. of China   Email: fxuehist@sina.com
,
Jimeng Ge
a   College of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453002, P. R. of China   Email: fxuehist@sina.com
,
Boshun Wan
c   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, P. R. of China   Email: bswan@dicp.ac.cn
› Author Affiliations
National Natural Science Foundation of China (21172218)
Further Information

Publication History

Received: 12 November 2019

Accepted after revision: 17 January 2020

Publication Date:
10 February 2020 (online)


Abstract

With chiral 2-methoxy-1-naphthylsulfinyl-based phenyl backbone sulfoxide-olefin ligands, a highly Rh-catalyzed addition of aryl­boronic acids to N,N-dimethylsulfamoyl-protected aldimines has been developed to afford a broad range of chiral diarylmethylamines in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Moreover, efficient enantioselective arylation of cyclic N-sulfonylimines was also achieved with excellent enantioselectivities (up to 98% ee).

Supporting Information

 
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