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    Por favor, use este identificador para citar o enlazar este ítem:https://uvadoc.uva.es/handle/10324/56004

    Título
    Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
    Autor
    Gil Ordóñez, MartaAutoridad UVA
    Aubry, Camille
    Niño, Cristopher
    Maestro Fernández, AliciaAutoridad UVA Orcid
    Andrés García, José MaríaAutoridad UVA Orcid
    Año del Documento
    2022
    Editorial
    MDPI
    Descripción
    Producción Científica
    Documento Fuente
    Molecules, 2022, vol. 27, n. 20, 6983
    Resumo
    A series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in enantioselective Mannich reactions with different 1,3-dicarbonyl compounds. This method provides a direct pathway to access the 4-amino-5-pyrazolone derivatives bearing a quaternary substituted stereocenter and containing two privileged structure motifs, the β-diketone and pyrazolinone substructures. The adducts were obtained in excellent yields (up to 90%) and enantioselectivities (up to 94:6 er) by employing a very low loading of 2 mol% of a quinine-derived bifunctional squaramide as an organocatalyst for a wide range of substrates. In addition, the utility of the obtained products was demonstrated through one step transformations to enantioenriched diheterocyclic systems (4-pyrazolyl-pyrazolone and 4-isoxazolyl-pyrazolone), potentially promising candidates for drug discovery.
    Palabras Clave
    Organocatalysis
    Organocatálisis
    Ketimines
    Cetiminas
    Pyrazolone
    Pirazolona
    ISSN
    1420-3049
    Revisión por pares
    SI
    DOI
    10.3390/molecules27206983
    Version del Editor
    https://www.mdpi.com/1420-3049/27/20/6983
    Propietario de los Derechos
    © 2022 The Authors
    Idioma
    eng
    URI
    https://uvadoc.uva.es/handle/10324/56004
    Tipo de versión
    info:eu-repo/semantics/publishedVersion
    Derechos
    openAccess
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    • CINQUIMA - Artículos de revista [162]
    • DEP67 - Artículos de revista [52]
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    Universidad de Valladolid

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