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Campo DC | Valor | Lengua/Idioma |
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dc.contributor.author | Calles, Maria | - |
dc.contributor.author | Puigcerver, Julio | - |
dc.contributor.author | Alonso, Diego A. | - |
dc.contributor.author | Alajarín, Mateo | - |
dc.contributor.author | Martinez-Cuezva, Alberto | - |
dc.contributor.author | Berná Cánovas, José | - |
dc.contributor.other | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica | es |
dc.date.accessioned | 2021-02-01T18:30:48Z | - |
dc.date.available | 2021-02-01T18:30:48Z | - |
dc.date.created | 2020 | - |
dc.date.issued | 2020-03-11 | - |
dc.identifier.citation | Chem. Sci., 2020, 11, 3629-3635. | es |
dc.identifier.issn | 2041-6520 | - |
dc.identifier.issn | 2041-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10201/102322 | - |
dc.description.abstract | 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. | es |
dc.format | application/pdf | es |
dc.format.extent | 7 | es |
dc.language | eng | es |
dc.publisher | Royal Society of Chemistry | es |
dc.relation | This work was supported by the MINECO and MICINN (CTQ2017-87231-P, RYC-2017-22700 and PGC2018-096616-BI00) with joint financing by FEDER Funds and Fundacion Seneca-CARM (Project 20811/PI/18). D. A. A. also thanks the University of Alicante for the financial support (VIGROB-173FI). The authors gratefully acknowledge the computer resources at Cibeles and the technical support provided by the Centro de Computacion Cientifica-UAM (RES-QSB-2019-3-0012). | es |
dc.relation.isreplacedby | https://doi.org/10.1039/D0SC00444H | es |
dc.rights | info:eu-repo/semantics/openAccess | es |
dc.subject | ASYMMETRIC ALDOL REACTION | es |
dc.subject | MECHANICAL BOND | es |
dc.subject | MOLECULAR RECOGNITION | es |
dc.subject | MICHAEL ADDITIONS | es |
dc.subject | ROTAXANE | es |
dc.subject | ORGANOCATALYSIS | es |
dc.subject.other | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica | es |
dc.title | Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes | es |
dc.type | info:eu-repo/semantics/article | es |
dc.relation.publisherversion | https://pubs.rsc.org/en/content/articlelanding/2020/sc/d0sc00444h | es |
dc.identifier.doi | 10.1039/D0SC00444H | - |
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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