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Stereocontrolled synthesis of -lactams within [2]rotaxanes: a showcase of the chemical consequences of the mechanical bonding

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dc.contributor.authorMartinez-Cuezva, Alberto
dc.contributor.authorLopez-Leonardo, Carmen
dc.contributor.authorBautista, Delia
dc.contributor.authorAlajarín, Mateo
dc.contributor.authorBerná Cánovas, José
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2021-11-03T17:23:09Z
dc.date.available2021-11-03T17:23:09Z
dc.date.issued2016-06-29
dc.description.abstractThe intramolecular cyclization of N-benzyl fumaramide [2]rotaxanes is described. The mechanical bond of these substrates activates this transformation to proceed in high yields and in a regio- and diastereoselective manner giving interlocked 3,4-disubstituted trans azetidin-2-ones. This activation effect differs from the common shielding stabilization of threaded functions through amide-based macrocycles promoting an unusual and disfavored 4-exo-trig ring closure. Further kinetic and synthetic studies allowed us to produce an original approach towards  -lactams through a one-pot protocol based on an intramolecular ring closure followed by a thermally-induced dethreading step. The advantages for carrying out this cyclization in the confined space of a benzylic amide macrocycle were attributed to the anchimeric assistance of the surrounding macrocycle.es
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dc.format.extent6es
dc.identifier.citationJ. Am. Chem. Soc. 2016, 138, 28, 8726–8729
dc.identifier.doi10.1021/jacs.6b05581
dc.identifier.issn0002-7863
dc.identifier.urihttp://hdl.handle.net/10201/113634
dc.languageenges
dc.publisherACSes
dc.relationNombre del proyecto: FUNCIONALIDAD Y SINTESIS DE MOLECULAS ENLAZADAS MECANICAMENTE. Código: CTQ2014-56887-P . Agencia/entidad financiadora: MINISTERIO DE ECONOMÍA, INDUSTRIA Y COMPETITIVIDAD. Ámbito Nacional. PROGRAMA ESTATAL DE FOMENTO DE LA INVESTIGACIÓN CIENTÍFICA Y TÉCNICA DE EXCELENCIA SUBPROGRAMA ESTATAL DE GENERACIÓN DE CONOCIMIENTO. Convocatoria 2014es
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/jacs.6b05581es
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectrotaxanees
dc.subjectcyclizationes
dc.subjectlactames
dc.subjectmacrocyclees
dc.subjectactivationes
dc.subject.otherCDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánicaes
dc.titleStereocontrolled synthesis of -lactams within [2]rotaxanes: a showcase of the chemical consequences of the mechanical bondinges
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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