Construction of Novel Tetrahydro--carboline-1-thione Spirooxindoles by BrOnsted Acid Mediated Formal [3+3] Cyclization of 3-Indolylmethanols with 3-Isothiocyanato Oxindoles

被引：7

作者：

Liao, Yijun ^{[1
,2
]}

Bai, Mei ^{[1
,2
]}

Yu, Shuowen ^{[1
,2
]}

Zhang, Minmin ^{[1
,2
]}

Hu, Fangzhi ^{[1
,2
]}

Xu, Xiaoying ^{[1
]}

Yuan, Weicheng ^{[1
]}

Zhang, Xiaomei ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China

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

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2017年 / 54卷 / 02期

基金：

中国国家自然科学基金;

关键词：

N-ACYLIMINIUM IONS; CATALYTIC ASYMMETRIC CONSTRUCTION; INTERMOLECULAR ADDITION-REACTIONS; ENANTIOSELECTIVE SYNTHESIS; CASCADE REACTION; 1,3-DIPOLAR CYCLOADDITION; POLYCYCLIC SPIROOXINDOLES; FUSED SPIROOXINDOLES; EFFICIENT SYNTHESIS; AZOMETHINE YLIDES;

D O I：

10.1002/jhet.2708

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

p-Toluenesulfonic acid mediated formal [3+3] cyclization of 3-indolylmethanols with 3-isothiocyanato oxindoles was realized. This transformation allowed for the synthesis of a series of novel tetrahydro--carboline-1-thione spirooxindoles in moderate to excellent yields (up to 99%) with generally good diastereoselectivities (up to >20:1). The structure of one product was determined by an X-ray crystal structural analysis.

引用

页码：1311 / 1317

页数：7

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