Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles.
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
15 Jul 2023
15 Jul 2023
Historique:
received:
07
01
2023
accepted:
03
07
2023
medline:
17
7
2023
pubmed:
16
7
2023
entrez:
15
7
2023
Statut:
epublish
Résumé
A carbene-catalyzed chemoselective reaction of unsymmetric enedials is disclosed. The reaction provides a concise access to bicyclic furo[2,3-b]pyrroles derivatives in excellent selectivity. A main challenge in this reaction is chemoselective reaction of the two aldehyde moieties in the enedial substrates. Mechanistic studies via experiments suggest that our chemoselectivity controls are mostly achieved on the reducing properties of different sited Breslow intermediates. Several side reactions processes and the corresponding side adducts are also studied by high resolution mass spectroscopy analysis. Our method allows for efficient assembly of the furo[2,3-b]pyrrole structural moieties and their analogues widely found in natural products and pharmaceuticals.
Identifiants
pubmed: 37454112
doi: 10.1038/s41467-023-39988-z
pii: 10.1038/s41467-023-39988-z
pmc: PMC10349821
doi:
Substances chimiques
Pyrroles
0
carbene
2465-56-7
Methane
OP0UW79H66
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4243Subventions
Organisme : National Natural Science Foundation of China (National Science Foundation of China)
ID : 21732002
Organisme : National Natural Science Foundation of China (National Science Foundation of China)
ID : 22061007
Organisme : National Natural Science Foundation of China (National Science Foundation of China)
ID : 22071036
Informations de copyright
© 2023. The Author(s).
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