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Asymmetric Pd-catalyzed allylic substitution using a large sugar-based monophosphite ligand library. Scope and limitations

  • Datos identificativos

    Identificador: PC:1256
    Autores:
    Montserrat DiéguezSabina AlegreYvette MataOscar Pàmies
    Resumen:
    We have applied a modular sugar-based phosphite ligand library for the Pd-catalyzed allylic substitution reactions of several substrates. These ligands are derived from D-(+)-glucose, D-(+)-galactose and D-(+)- fructose, which lead to a wide range of sugar backbones, and contain several substituents at the C-3 carbon of the furanoside backbone and several substituents/ configurations in the biaryl moiety, with different steric and electronic properties. Systematic variation of the ligand parameters indicates that the catalytic performance (activities and enantioselectivities) is highly affected by sugar backbone, the substituents at the C-3 carbon of the furanoside backbone, the configurations at the C-3 and C-4 carbons of the ligand backbone and the type of substituents/configurations in the biaryl phosphite moiety as well as the substrate type. For disubstituted substrates moderate enantioselectivities (up to 72%) were achieved using ligand L8d, while for monosubstituted substrates the highest enantioselectivities (up to 40%) were obtained using ligand L9a
  • Otros:

    Autor según el artículo: Montserrat Diéguez Sabina Alegre Yvette Mata Oscar Pàmies
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: DIÉGUEZ FERNÁNDEZ, MONTSERRAT Sabina Alegre Yvette Mata PAMIES OLLÉ, OSCAR
    Palabras clave: asymmetric catalysis palladium allylic substitution
    Resumen: We have applied a modular sugar-based phosphite ligand library for the Pd-catalyzed allylic substitution reactions of several substrates. These ligands are derived from D-(+)-glucose, D-(+)-galactose and D-(+)- fructose, which lead to a wide range of sugar backbones, and contain several substituents at the C-3 carbon of the furanoside backbone and several substituents/ configurations in the biaryl moiety, with different steric and electronic properties. Systematic variation of the ligand parameters indicates that the catalytic performance (activities and enantioselectivities) is highly affected by sugar backbone, the substituents at the C-3 carbon of the furanoside backbone, the configurations at the C-3 and C-4 carbons of the ligand backbone and the type of substituents/configurations in the biaryl phosphite moiety as well as the substrate type. For disubstituted substrates moderate enantioselectivities (up to 72%) were achieved using ligand L8d, while for monosubstituted substrates the highest enantioselectivities (up to 40%) were obtained using ligand L9a
    Grupo de investigación: Organometàl.lics i Catàlisi Homogènia
    Áreas temáticas: Química Química Chemistry
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 2300-4630
    Identificador del autor: 0000-0002-8450-0656 n/a n/a 0000-0002-2352-8508
    Fecha de alta del registro: 2015-11-18
    Página final: 39
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Enlace a la fuente original: http://www.degruyter.com/view/j/asorg.2014.1.issue-1/asorg-2014-0001/asorg-2014-0001.xml
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI del artículo: 10.2478/asorg-2014-0001
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2014
    Página inicial: 32
    Tipo de publicación: Article
  • Palabras clave:

    Catàlisi asimètrica
    Pal·ladi (Element químic)
    asymmetric catalysis
    palladium
    allylic substitution
    Química
    Química
    Chemistry
    2300-4630
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