Site-Selective, Photocatalytic Vinylogous Amidation of Enones

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Authors
Szabó, Kitti Franciska
Goliszewska, Katarzyna
Szurmak, Jakub
Rybicka-Jasińska, Katarzyna
Gryko, Dorota
Date
2022
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
License
Creative Commons License
Creative Commons Attribution 4.0 International License
Abstract
Despite the broad interest in organic compounds possessing a γ-aminocarbonyl motif, limited strategies for their synthesis have been reported. Herein, we describe a mild and efficient method for the site-selective amidation of unsaturated enones with electrophilic N-centered radicals as a key intermediate. The photocatalytic vinylogous reaction of dienolates with N-amino pyridinium salts affords γ-amido carbonyl compounds. This process is high-yielding, scalable, and tolerates a broad range of unsaturated α,β-unsaturated carbonyls, including biologically relevant compounds, as starting materials.
Description
Citation
Org. Lett. 2022, 24, 44, 8120–8124 ; https://doi.org/10.1021/acs.orglett.2c03161
URI
https://depot.ceon.pl/handle/123456789/21871
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