Stereospecific Photoredox-Catalyzed Vinylations to Functionalized Alkenes and C-Glycosides.
Alkenes
Glycosides
Hypervalent Iodine Compounds
Photoredox Catalysis
Vinylbenziodoxolones
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
08 May 2023
08 May 2023
Historique:
received:
27
01
2023
medline:
16
3
2023
pubmed:
16
3
2023
entrez:
15
3
2023
Statut:
ppublish
Résumé
We report an efficient radical-mediated C-C coupling through photoredox-catalyzed reactions of 4-alkyl-dihydropyridines (DHPs) and vinylbenziodoxol(on)es (VBX, VBO). This transition-metal-free and mild photocatalytic method has excellent functional group tolerance and affords vinylated products in good yields, with complete retention of the alkene configuration. The utility of the methodology is demonstrated by the diastereoselective synthesis of C-vinyl glycosides. Preliminary mechanistic studies suggest that the C-C bond formation is stereospecific and proceeds through a concerted radical coupling transition state.
Identifiants
pubmed: 36920275
doi: 10.1002/anie.202301368
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301368Subventions
Organisme : Wenner-Gren Stiftelserna
ID : UPD 2020-0144
Organisme : Wenner-Gren Stiftelserna
ID : UPD 2021-0097
Organisme : Vetenskapsrådet
ID : 2019-04232
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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See the Supporting Information for details.
Only one alkene isomer was detected by 1H NMR. We have described this as E/Z>20 : 1 due to the detection limits of the analysis method.
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Deposition Numbers 2208589 and 2223265 contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
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