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Título: | Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes |
Fecha de publicación: | 24-ene-2024 |
Editorial: | American Chemical Society |
Cita bibliográfica: | Journal of the American Chemical Society (JACS) 2024, 146, pp.2882−2887 |
Resumen: | 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. |
Autor/es principal/es: | Puigcerver, Julio Marin-Luna, Marta Iglesias-Sigüenza, Javier Alajarin, Mateo Martinez-Cuezva, Alberto Berna, Jose |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica |
Versión del editor: | https://pubs.acs.org/doi/10.1021/jacs.3c11611 |
URI: | http://hdl.handle.net/10201/139945 |
DOI: | https://doi.org/10.1021/jacs.3c11611 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 6 |
Derechos: | info:eu-repo/semantics/openAccess Atribución 4.0 Internacional |
Descripción: | © 2024. The authors. This document is made available under the CC-BY 4.0 license http://creativecommons.org/licenses/by /4.0/ This document is the published version of a published work that appeared in final form in Journal of the American Chemical Society (JACS). To access the final work, see DOI: https://doi.org/10.1021/jacs.3c11611 |
Aparece en las colecciones: | Artículos: Química Orgánica |
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