Publication:
Reactivity of Glutaconamides Within [2]Rotaxanes: Mechanical Bond Controlled Chemoselective Synthesis of Highly Reactive α-Ketoamides and their Light-Triggered Cyclization

Thumbnail Image
Files
Angew Chem Int Ed - 2023 - Maria Perez - Reactivity of Glutaconamides Within 2 Rotaxanes Mechanical Bond Controlled.cleaned.pdf(4.12 MB)
Date
2023-03-23
relationships.isAuthorOfPublication
relationships.isSecondaryAuthorOf
relationships.isDirectorOf
Authors
Perez, Jesus de Maria ; Alajarin, Mateo ; Martinez-Cuezva, Alberto ; Berna, Jose
item.page.secondaryauthor
item.page.director
Publisher
German Chemical Society
publication.page.editor
publication.page.department
Química Orgánica
DOI
https://doi.org/10.1002/anie.202302681
item.page.type
info:eu-repo/semantics/article
Description
Abstract
Glutaconamide-based [2]rotaxanes are efficiently oxidized to the respective interlocked α-ketoamides, whereas their non-interlocked threads afford hydroxycyclohexene tetraamides under similar reaction conditions. These results showcase the mechanically interlocking of highly reactive substrates as a powerful tool for controlling their chemical behavior. Inside the macrocycle and under irradiation with light, the α-ketoamide threads convert, in a divergent manner, into the corresponding interlocked hydroxy-β-lactams or oxazolidinones by two modes of Norrish/Yang type-II intramolecular cyclizations, processes that are efficiently chemocontrolled by the mechanical bond.
publication.page.subject
Citation
Angewandte Chemie International EditionVolume 62, Issue 21 e202302681
URI
http://hdl.handle.net/10201/135166
item.page.embargo
Collections
Artículos
Ir a Estadísticas