dc.creator | Puigcerver, Julio | es |
dc.creator | Marín Luna, Marta | es |
dc.creator | Iglesias Sigüenza, Francisco Javier | es |
dc.creator | Alajarin, Mateo | es |
dc.creator | Martinez-Cuezva, Alberto | es |
dc.creator | Berna, Jose | es |
dc.date.accessioned | 2024-06-24T10:48:11Z | |
dc.date.available | 2024-06-24T10:48:11Z | |
dc.date.issued | 2024-01-24 | |
dc.identifier.citation | Puigcerver, J., Marín Luna, M., Iglesias Sigüenza, F.J., Alajarin, M., Martinez-Cuezva, A. y Berna, J. (2024). Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes. Journal of the American Chemical Society, 146 (5), 2882-2887. https://doi.org/10.1021/jacs.3c11611. | |
dc.identifier.issn | 0002-7863 | es |
dc.identifier.issn | 1520-5126 | es |
dc.identifier.uri | https://hdl.handle.net/11441/160805 | |
dc.description.abstract | Herein we describe an effective transmission of chirality, from mechanically planar chirality to point chirality, in hydrogen-bonded [2]rotaxanes. A highly selective mono-N-methylation of one (out of four) amide N atom at the macrocyclic counterpart of starting achiral rotaxanes generates mechanically planar chirality. Followed by chiral resolution, both enantiomers were subjected to a base-promoted intramolecular cyclization, where their interlocked threads were transformed into new lactam moieties. As a matter of fact, the mechanically planar chiral information was effectively transferred to the resulting stereocenters (covalent chirality) of the newly formed heterocycles. Upon removing the entwined macrocycle, the final lactams were obtained with high enantiopurity. | es |
dc.description.sponsorship | Ministerio de Ciencia e Innovación y Agencia Estatal de Investigación de España - PID2019-106358GB-C22 y PID2020-113686GB | es |
dc.description.sponsorship | Fundación Séneca-CARM de Murcia, España. - 21907/PI/22 | es |
dc.format | application/pdf | es |
dc.format.extent | 6 p. | es |
dc.language.iso | eng | es |
dc.publisher | American Chemical Society | es |
dc.relation.ispartof | Journal of the American Chemical Society, 146 (5), 2882-2887. | |
dc.rights | Atribución 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
dc.title | Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes | es |
dc.type | info:eu-repo/semantics/article | es |
dc.type.version | info:eu-repo/semantics/publishedVersion | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química orgánica | es |
dc.relation.projectID | PID2019-106358GB-C22 | es |
dc.relation.projectID | PID2020-113686GB | es |
dc.relation.projectID | Fundación Séneca-CARM 21907/PI/22 | es |
dc.relation.publisherversion | https://doi.org/10.1021/jacs.3c11611 | es |
dc.identifier.doi | 10.1021/jacs.3c11611 | es |
dc.journaltitle | Journal of the American Chemical Society | es |
dc.publication.volumen | 146 | es |
dc.publication.issue | 5 | es |
dc.publication.initialPage | 2882 | es |
dc.publication.endPage | 2887 | es |
dc.contributor.funder | Ministerio de Ciencia e Innovación (MICIN). España | es |
dc.contributor.funder | Agencia Estatal de Investigación. España | es |
dc.contributor.funder | Fundación Séneca-CARM, Murcia, España. | es |