Synthesis 2022; 54(21): 4703-4710
DOI: 10.1055/a-1588-0072
special topic
Asymmetric C–H Functionalization

Ruthenium(II)/Chiral Carboxylic Acid Catalyzed Enantioselective C–H Functionalization of Sulfoximines

Long-Tao Huang
a   Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12 Nishi-6, Sapporo, Hokkaido 060-0812, Japan
,
Yuki Hirata
a   Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12 Nishi-6, Sapporo, Hokkaido 060-0812, Japan
,
Yoshimi Kato
a   Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12 Nishi-6, Sapporo, Hokkaido 060-0812, Japan
,
b   Global Station for Biosurfaces and Drug Discovery, Global Institution for Collaborative Research and Education (GI-CoRE), Hokkaido University, Kita-12 Nishi-6, Sapporo, Hokkaido 060-0812, Japan
c   Zhang Dayu School of Chemistry, Dalian University of Technology, Dalian 116024, P. R. of China   linluqing@dlut.edu.cn
,
a   Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12 Nishi-6, Sapporo, Hokkaido 060-0812, Japan
,
a   Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12 Nishi-6, Sapporo, Hokkaido 060-0812, Japan
,
a   Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12 Nishi-6, Sapporo, Hokkaido 060-0812, Japan
b   Global Station for Biosurfaces and Drug Discovery, Global Institution for Collaborative Research and Education (GI-CoRE), Hokkaido University, Kita-12 Nishi-6, Sapporo, Hokkaido 060-0812, Japan
› Author Affiliations
This work was supported in part by the Japan Society for the Promotion of Science (JSPS; KAKENHI grant number JP20H02730 and JP20H04794 in Hybrid Catalysis).


Abstract

Ruthenium(II)-catalyzed enantioselective C–H functionalization reactions of sulfoximines with sulfoxonium ylides are described. The combination of [RuCl2(p-cymene)]2 and a pseudo-C 2-symmetric binaphthyl monocarboxylic acid furnished the S-chiral products in 76:24 to 92:8 er.

Supporting Information



Publication History

Received: 13 July 2021

Accepted after revision: 16 August 2021

Accepted Manuscript online:
16 August 2021

Article published online:
11 October 2021

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