Bronsted acid-catalyzed regioselective reactions of 2-indolylmethanols with cyclic enaminone and anhydride leading to C3-functionalized indole derivatives

被引：43

作者：

Li, Can ^{[1
]}

Zhang, Hong-Hao ^{[1
]}

Fan, Tao ^{[1
]}

Shen, Yang ^{[1
]}

Wu, Qiong ^{[2
]}

Shi, Feng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

[2] Xuzhou Inst Technol, Sch Chem & Chem Engn, Xuzhou 221111, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 29期

关键词：

TETRAHYDRO-BETA-CARBOLINE; ENANTIOSELECTIVE SYNTHESIS; ALPHA-ALKYLATION; ORGANOCATALYTIC CONSTRUCTION; INDOL-2-YL CARBINOLS; S(N)1-TYPE REACTION; TERTIARY ALCOHOLS; 4+3 CYCLOADDITION; CASCADE REACTIONS; ALDEHYDES;

D O I：

10.1039/c6ob01282e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An abnormal regioselective substitution of 2-indolylmethanols with nucleophiles such as cyclic enaminone and cyclic anhydride has been established in the presence of Bronsted acid, which efficiently afforded C3-functionalized indole derivatives with structural diversity in high yield and regiospecificity (40 examples, up to 99% yield). Using this approach, the reactivity of the C3-position of the indole was switched from nucleophilic to electrophilic, which could serve as an "umpolung" strategy in organic synthesis.

引用

页码：6932 / 6936

页数：5

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