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

doi:10.1055/s-0037-1610749

Synthesis, Table of Contents

Synthesis 2020; 52(10): 1498-1511
DOI: 10.1055/s-0037-1610749

paper

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

Feng Xue∗

^aCollege of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453002, P. R. of China Email: fxuehist@sina.com

,

Qibin Liu ∗

^bDalian Allychem Co., Ltd, 5 Jinbin Road, Dalian 116620, P. R. of China Email: qliu@allychem.com

,

Yong Zhu

^aCollege of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453002, P. R. of China Email: fxuehist@sina.com

,

Yifei Huang

^aCollege of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453002, P. R. of China Email: fxuehist@sina.com

,

Jimeng Ge

^aCollege of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453002, P. R. of China Email: fxuehist@sina.com

,

Boshun Wan∗

^cDalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, P. R. of China Email: bswan@dicp.ac.cn

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Abstract

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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).

Key words

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

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References

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16 We tried several experiments in which stoichiometric reactions between the ligand 1 and [RhCl(C₂H₄)]₂ were conducted and the results were further checked through ¹H NMR spectroscopy. The free olefin of the Ligand 1 was characterized by the presence in the ¹H NMR spectrum of two doublets at 7.03 (H_a, J = 16 Hz) and 7.41 (H_b, J = 16 Hz) ppm. When the reaction was finished, the olefin was still present in the ¹H NMR spectrum of two doublets at 7.03 (H_a, J = 16 Hz) and 7.41 (H_b, J = 16 Hz) ppm, which indicated that the ligand does not bind to the metal to show no appreciable reactivity in catalysis. Refer to Supporting Information (Page S106) for details.
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Supplementary Material

Supporting Information