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Título: | Photoswitchable interlocked thiodiglycolamide as a cocatalyst of a chalcogeno-Baylis–Hillman reaction |
Fecha de publicación: | 7-mar-2017 |
Fecha de defensa / creación: | 2017 |
Editorial: | Royal Society of Chemistry |
Cita bibliográfica: | Chemical Science, 8, 2017, 3775-3780 |
ISSN: | Electronic: 2041-6539 Print: 2041-6520 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | Chalcogeno-Baylis–Hillman reaction Rotaxane catalysts Mechanical bond |
Resumen: | En route to a photoswitchable interlocked catalyst we have proved the ability of thiodiglycolamide to act as a template in the formation of hydrogen-bonded [2]rotaxanes. X-ray diffraction studies reveal the shielding of the sulfide atom by the macrocycle. A series of molecular shuttles are described as having an isomerizable fumaramide and thiodiglycolamide binding sites for controlling the relative ring position at will. By employing these systems as photoregulated catalysts, the TiCl4-mediated chalcogeno-Morita–Baylis–Hillman reaction is tested. In the presence of the maleamide shuttle, in which the sulfide function is encapsulated by the macrocycle, a complete loss in control of the geometry of the produced aldol is observed. The E-aldol adduct is predominantly obtained when the photoisomerized fumaramide shuttle, in which the sulfide function is exposed, is used. |
Autor/es principal/es: | Martinez-Cuezva, Alberto Saura Sanmartín, Adrián Nicolas-Garcia, Tomas Navarro, Cristian Orenes, Raul-Angel Alajarín, Mateo Berná, José |
Director/es: | Berná, José |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica |
URI: | http://hdl.handle.net/10201/135783 |
DOI: | https://doi.org/10.1039/C7SC00724H |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 6 |
Derechos: | info:eu-repo/semantics/openAccess Atribución 4.0 Internacional |
Descripción: | © 2017. The Authors. This manuscript version is made available under the CC-BY 4.0 license https://creativecommons.org/licenses/by/4.0/ This document is the Published Manuscript version of a Published Work that appeared in final form in Chemical Science. To access the final edited and published work see https://doi.org/10.1039/C7SC00724H |
Aparece en las colecciones: | Artículos: Química Orgánica |
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