A highly enantioselective thiolation of sulfonyl indoles to access 3-sec-sulfur-substituted indoles in water

Ping Chen; Sheng-mei Lu; Wengang Guo; Yan Liu; Can Li

doi:10.1039/c5cc07721d

A highly enantioselective thiolation of sulfonyl indoles to access 3-sec-sulfur-substituted indoles in water

Chem Commun (Camb). 2016 Jan 4;52(1):96-9. doi: 10.1039/c5cc07721d.

Authors

Ping Chen¹, Sheng-mei Lu², Wengang Guo¹, Yan Liu², Can Li²

Affiliations

¹ State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China. yanliu503@dicp.ac.cn canli@dicp.ac.cn and Graduate University of Chinese Academy of Sciences, Beijing 100049, China.
² State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China. yanliu503@dicp.ac.cn canli@dicp.ac.cn.

PMID: 26497910
DOI: 10.1039/c5cc07721d

Abstract

A highly enantioselective approach for the synthesis of 3-alkyl- indole or indoline derivatives with a functional thiol group is presented. The chemistry is based on the asymmetric 1,4-addition of thiol to vinylogous imine intermediates, which are generated in situ from sulfonylindoles. The broad substrate transformation proceeds with high yields (up to 96%) and enantioselectivity (up to 98% ee) in a water-compatible system.

Publication types

Research Support, Non-U.S. Gov't