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

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dc.contributor.authorPerez, Jesus de Maria
dc.contributor.authorAlajarin, Mateo
dc.contributor.authorMartinez-Cuezva, Alberto
dc.contributor.authorBerna, Jose
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2023-10-26T11:30:09Z
dc.date.available2023-10-26T11:30:09Z
dc.date.issued2023-03-23
dc.description.abstractGlutaconamide-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.es
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dc.format.extent6es
dc.identifier.citationAngewandte Chemie International EditionVolume 62, Issue 21 e202302681
dc.identifier.doihttps://doi.org/10.1002/anie.202302681
dc.identifier.issn1521-3773
dc.identifier.urihttp://hdl.handle.net/10201/135166
dc.languageenges
dc.publisherGerman Chemical Societyes
dc.relationSpanish Ministry of Science and Innovation (project PID2020-113686GB-I00/MICINN/AEI/10.13039/501100011033) Fundacion Seneca-CARM (project 21907/PI/22).es
dc.relation.requireshttp://hdl.handle.net/10201/135143
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución 4.0 Internacional*
dc.rightsAtribución-NoComercial 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/*
dc.titleReactivity of Glutaconamides Within [2]Rotaxanes: Mechanical Bond Controlled Chemoselective Synthesis of Highly Reactive α-Ketoamides and their Light-Triggered Cyclizationes
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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