Chiral Lewis Base/Achiral Acid Co-Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides

Qin Yang; Hui-Yun Luo; Deng Zhu; Xin-Yu Zhang; Hua Ke; Zhi-Min Chen

doi:10.1002/cjoc.202400255

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (17) : 2005 -2009. DOI: 10.1002/cjoc.202400255

Concise Report

Chiral Lewis Base/Achiral Acid Co-Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides

Author information +

History +

PDF

Abstract

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.

Keywords

Electrophilic substitution / Desymmetrization / Kinetic resolution / Atropisomerism / Asymmetric catalysis / Heterocycles

Cite this article

Download citation ▾

Qin Yang, Hui-Yun Luo, Deng Zhu, Xin-Yu Zhang, Hua Ke, Zhi-Min Chen. Chiral Lewis Base/Achiral Acid Co-Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides. Chinese Journal of Chemistry, 2024, 42(17): 2005-2009 DOI:10.1002/cjoc.202400255