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
收藏
页码：96 / 99
页数：4
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