Chiral Lewis Base/Achiral Acid Co-Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides
Qin Yang
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorHui-Yun Luo
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorDeng Zhu
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorXin-Yu Zhang
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Hua Ke
Engineering Technology Research Center for Environmental Protection Materials, Pingxiang University, Pingxiang, Jiangxi, 337055 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Zhi-Min Chen
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, 730000 China
E-mail: [email protected]; [email protected]Search for more papers by this authorQin Yang
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorHui-Yun Luo
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorDeng Zhu
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorXin-Yu Zhang
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Hua Ke
Engineering Technology Research Center for Environmental Protection Materials, Pingxiang University, Pingxiang, Jiangxi, 337055 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Zhi-Min Chen
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240 China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, 730000 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
Chiral BINAM-derived selenide/achiral acid co-catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time. A variety of C—N axially chiral sulfur-containing pyrrole derivatives were readily obtained in moderate to good yields with moderate to excellent enantioselectivities. This catalytic system involves sequential desymmetrization and kinetic resolution.
Supporting Information
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Appendix S1: Supporting Information |
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- 8CCDC 2280030 (compound 3a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cam-bridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.