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

被引：23

作者：

Chen, Ping ^{[1
,2
]}

Lu, Sheng-mei ^{[1
]}

Guo, Wengang ^{[1
,2
]}

Liu, Yan ^{[1
]}

Li, Can ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 01期

基金：

中国国家自然科学基金;

关键词：

CARBON-CARBON BOND; BETA-SUBSTITUTED TRYPTOPHANS; FRIEDEL-CRAFTS REACTION; GENERATED IN-SITU; CONJUGATE ADDITION; TRANSFER HYDROGENATION; ARYLSULFONYL INDOLES; EMULSION DROPLETS; MICHAEL ADDITION; AQUEOUS-MEDIA;

D O I：

10.1039/c5cc07721d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective approach for the synthesis of 3-alkylindole 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.

引用

页码：96 / 99

页数：4

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