New opportunities in the stereoselective dearomatization of indoles

被引：30

作者：

Manoni, Elisabetta ^{[1
]}

De Nisi, Assunta ^{[1
]}

Bandini, Marco ^{[1
]}

机构：

[1] Alma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, Via Selmi 2, I-40126 Bologna, Italy

来源：

PURE AND APPLIED CHEMISTRY | 2016年 / 88卷 / 03期

关键词：

asymmetric catalysis; Bronsted acid; dearomatization; ESOC-19; gold; indole; GOLD-CATALYZED REACTIONS; ORGANIC-SYNTHESIS; CYCLOADDITION REACTIONS; NATURAL-PRODUCTS; METAL-FREE; ALLENAMIDES; ACTIVATION; CHEMISTRY; PLATINUM; LIGANDS;

D O I：

10.1515/pac-2016-0101

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The regio- and stereoselective dearomatization of indoles is realized for the first time by combining readily available indolyl precursors and electron-rich allenes, namely allenamides and aryloxyallenes. Inter- as well as intramolecular condensations were realized under gold and Bronsted acid catalysis providing a range of densely functionalized indoline and indolenine cores in high yields and excellent stereochemical outcome. Chemodivergent reaction profiles (Micheal-type addition vs. [2 + 2]-cycloaddition) were realized by a tailored design of both reaction conditions and functionalization of the reaction partners.

引用

页码：207 / 214

页数：8

共 55 条

[1] Exploiting [2+2] cycloaddition chemistry: achievements with allenes [J].