A highly enantioselective thiolation of sulfonyl indoles to access 3-sec-sulfur-substituted indoles in water.
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.
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.
Ping
P
Chen
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.
Sheng-mei
SM
Lu
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.
Wengang
W
Guo
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.
Yan
Y
Liu
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.
Can
C
Li