Dearomatization of 3-Nitroindoles with Highly γ-Functionalized Allenoates in Formal (3+2) Cycloadditions.
allenoate
annulation
dearomatization
density functional calculation
nitrondole
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
28 Oct 2019
28 Oct 2019
Historique:
received:
29
07
2019
revised:
03
09
2019
pubmed:
12
9
2019
medline:
12
9
2019
entrez:
12
9
2019
Statut:
ppublish
Résumé
3-Nitroindoles are easily reacted with highly substituted γ-allenoates in the presence of a commercially available phosphine catalyst. For instance, allenoates derived from biomolecules such as amino and deoxycholic acids are combined for the first time with 3-nitroindole. The corresponding dearomatized (3+2) tricyclic cycloadducts are obtained as α-regioisomers exclusively. DFT computations shed light on this multi-step reaction mechanism and on the selectivities observed in the sequence.
Identifiants
pubmed: 31507002
doi: 10.1002/chem.201903455
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
13688-13693Subventions
Organisme : Agence Nationale pour la Recherche
ID : ANR-17-CE07-0050
Organisme : Labex SynOrg
ID : ANR-11-LABX-0029
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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