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
收藏
页码：6932 / 6936
页数：5
相关论文
共 50 条
12345