Dearomative (3+2) Cycloadditions of Unprotected Indoles

被引：12
|
作者：
Ryckaert, Bram [1 ]
Hullaert, Jan [1 ]
Van Hecke, Kristof [2 ]
Winne, Johan M. [1 ]
机构：
[1] Univ Ghent, Dept Organ & Macromol Chem, B-9000 Ghent, Belgium
[2] Univ Ghent, Dept Chem, B-9000 Ghent, Belgium
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 23期
基金：
比利时弗兰德研究基金会;
关键词：
ALLYL CATIONS; 3-NITROINDOLES; ANNULATION; IONS;
D O I：
10.1021/acs.orglett.2c01214
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The (3 + 2) cycloaddition of various indoles with a dithioallyl cation affords dearomatized cyclopentannulated adducts, with complete control of regioselectivity and excellent chemo- and diastereoselectivity. The success of the reaction critically relies on the use of an excess of very strong Bronsted acid, which paradoxically prevents carbocationic side reactions. The reaction tolerates sensitive functionalities such as basic amines or free hydroxyls, and we demonstrate its use in late stage derivatization of highly functionalized, unprotected indoles.
引用
收藏
页码：4119 / 4123
页数：5
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