Organocatalytic Asymmetric Dearomatization of 3-Nitroindoles and 3-Nitrobenzothiophenes via Thiol-Triggered Diastereo- and Enantioselective Double Michael Addition Reaction

被引：41

作者：

Chen, Xin-Meng ^{[1
,3
]}

Lei, Chuan-Wen ^{[1
,3
]}

Yue, Deng-Feng ^{[1
,3
]}

Zhao, Jian-Qiang ^{[2
]}

Wang, Zhen-Hua ^{[2
]}

Zhang, Xiao-Mei ^{[1
]}

Xu, Xiao-Ying ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Sichuan, Peoples R China

[2] Chengdu Univ, Inst Adv Study, Chengdu 610106, Sichuan, Peoples R China

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

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 14期

关键词：

3+2 CYCLOADDITION REACTION; 3-ISOTHIOCYANATO OXINDOLES; CASCADE REACTION; INDOLES; ACCESS; DERIVATIVES; STRATEGIES; CATALYSIS;

D O I：

10.1021/acs.orglett.9b01688

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organocatalytic asymmetric dearomatization of 3-nitroindoles and 3-nitrobenzothiophenes by reaction with ethyl 4-mercapto-2-butenoate has been developed. A range of chiral tetrahydrothiopheneindolines and tetrahydrothiophene-benzothiophenes bearing three contiguous stereocenters are obtained in high yields with good diastereoselectivities and excellent enantioselectivities. This is the first example of thiol-triggered catalytic asymmetric dearomatization of 3-nitroindoles and 3-nitrobenzothiophenes.

引用

页码：5452 / 5456

页数：5

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