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
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

Pagination

4119-4123

Auteurs

Bram Ryckaert (B)

Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, B-9000 Ghent, Belgium.

Jan Hullaert (J)

Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, B-9000 Ghent, Belgium.

Kristof Van Hecke (K)

Department of Chemistry, Ghent University, Krijgslaan 281-S3, B-9000 Ghent, Belgium.

Johan M Winne (JM)

Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, B-9000 Ghent, Belgium.

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Classifications MeSH