Dearomative (3 + 2) Cycloadditions of Unprotected Indoles.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
17 06 2022
17 06 2022
Historique:
pubmed:
9
6
2022
medline:
22
6
2022
entrez:
8
6
2022
Statut:
ppublish
Résumé
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 Brønsted 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.
Identifiants
pubmed: 35674713
doi: 10.1021/acs.orglett.2c01214
doi:
Substances chimiques
Acids
0
Amines
0
Cations
0
Indoles
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM