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

Feng Xue*, Qibin Liu*, Yong Zhu, Yifei Huang, Jimeng Ge, Boshun Wan*

*Henan Institute of Science and Technology, Xinxiang 453002; Dalian Allychem Co., Ltd, Dalian 116620; Dalian Institute of Chemical Physics, Dalian 116023, P. R. of China, Email: fxuehistsina.com, qliuallychem.com, bswandicp.ac.cn

F. Xue, Q. Liu, Y. Zhu, Y. Huang, J. Ge, B. Wan, Synthesis, 2020, 52, 1498-1511.

DOI: 10.1055/s-0037-1610749

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Abstract

Chiral 2-methoxy-1-naphthylsulfinyl-based phenyl backbone sulfoxide-olefin ligands enable highly enantioselective Rh-catalyzed additions of aryl­boronic acids to N,N-dimethylsulfamoyl-protected aldimines to afford a broad range of chiral diarylmethylamines in high yields with excellent enantioselectivities. Moreover, efficient enantioselective arylation of cyclic N-sulfonylimines was also achieved.

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Key Words

diarylmethylamines, arylboronic acids, N,N-dimethylsulfamoyl-protected aldimines, sulfoxide-olefin ligands, asymmetric catalysis

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ID: J66-Y2020