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10.1039/D0SC00444H
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Título: | Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes |
Fecha de publicación: | 11-mar-2020 |
Fecha de defensa / creación: | 2020 |
Editorial: | Royal Society of Chemistry |
Cita bibliográfica: | Chem. Sci., 2020, 11, 3629-3635. |
ISSN: | 2041-6520 2041-6539 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | ASYMMETRIC ALDOL REACTION MECHANICAL BOND MOLECULAR RECOGNITION MICHAEL ADDITIONS ROTAXANE ORGANOCATALYSIS |
Resumen: | The synthesis of a pair of switchable interlocked prolinamides and their use as organocatalysts in three different enamine-activated processes are reported. A diacylaminopyridine moiety was incorporated into the thread for directing [2]rotaxane formation further allowing the association of complementary small molecules. The rotaxane-based systems were tested as organocatalysts in asymmetric enamine-mediated processes, revealing a significantly improved catalytic ability if compared with the non-interlocked thread. The presence of an electron-withdrawing nitro group at the macrocycle helps to achieve high conversions and enantioselectivities. These systems are able to interact with N-hexylthymine as a cofactor to form supramolecular catalysts displaying a divergent catalytic behaviour. The presence or absence of the cofactor controls the chemoselectivity in competitive reactions. |
Autor/es principal/es: | Calles, Maria Puigcerver, Julio Alonso, Diego A. Alajarín, Mateo Martinez-Cuezva, Alberto Berná Cánovas, José |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica |
Versión del editor: | https://pubs.rsc.org/en/content/articlelanding/2020/sc/d0sc00444h |
URI: | http://hdl.handle.net/10201/102322 |
DOI: | 10.1039/D0SC00444H |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 7 |
Derechos: | info:eu-repo/semantics/openAccess |
Aparece en las colecciones: | Artículos: Química Orgánica |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
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Chem_Sci_2020_DAP-Interlocked Prolinamides.pdf | 564,64 kB | Adobe PDF | Visualizar/Abrir |
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