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

  • Dades identificatives

    Identificador: PC:1256
    Autors:
    Montserrat DiéguezSabina AlegreYvette MataOscar Pàmies
    Resum:
    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
  • Altres:

    Autor segons l'article: Montserrat Diéguez Sabina Alegre Yvette Mata Oscar Pàmies
    Departament: Química Física i Inorgànica
    Autor/s de la URV: DIÉGUEZ FERNÁNDEZ, MONTSERRAT Sabina Alegre Yvette Mata PAMIES OLLÉ, OSCAR
    Paraules clau: asymmetric catalysis palladium allylic substitution
    Resum: 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
    Grup de recerca: Organometàl.lics i Catàlisi Homogènia
    Àrees temàtiques: Química Química Chemistry
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 2300-4630
    Identificador de l'autor: 0000-0002-8450-0656 n/a n/a 0000-0002-2352-8508
    Data d'alta del registre: 2015-11-18
    Pàgina final: 39
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: http://www.degruyter.com/view/j/asorg.2014.1.issue-1/asorg-2014-0001/asorg-2014-0001.xml
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.2478/asorg-2014-0001
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2014
    Pàgina inicial: 32
    Tipus de publicació: Article
  • Paraules clau:

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