Articles producció científica> Química Física i Inorgànica

Theoretical and Experimental Optimization of a New Amino Phosphite Ligand Library for Asymmetric Palladium-Catalyzed Allylic Substitution

  • Datos identificativos

    Identificador: PC:2568
    Autores:
    Maria BioscaMarc MagrePer-Ola NorrbyOscar PàmiesMontserrat Diéguez
    Resumen:
    Filiació URV: SIInclòs a la memòria: SI
  • Otros:

    Autor según el artículo: Maria Biosca; Marc Magre; Per-Ola Norrby; Oscar Pàmies; Montserrat Diéguez
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: BIOSCA BRULL, MARIA; Marc Magre; Per-Ola Norrby; PAMIES OLLÉ, OSCAR; DIÉGUEZ FERNÁNDEZ, MONTSERRAT
    Palabras clave: DFT calculations allylic substitution palladium
    Resumen: A new library of modular amino phosphite ligands obtained in a few synthetic steps from enantiopure amino alcohols has been tested in asymmetric Pd-catalyzed allylic substitution. The modular ligand design is crucial to find highly selective catalysts for each substrate type using a wide range of C-, N-, and O-nucleophiles. A DFT study of the species responsible for the enantiocontrol was used to optimize the ligand structure. By selecting the ligand components, we were able to identify unprecedented catalytic systems that can create new chiral C-C, C-N, and C-O bonds in a variety of substrate types (hindered and unhindered) in high yields and enantioselectivities (ee values up to 99 %). Further studies on the Pd-π-allyl intermediates provided a deep understanding of the effect of ligand structure in the origin of enantioselectivity. Potential applications of the new Pd/amino phosphite catalysts were demonstrated by the practical synthesis of a range of chiral carbocycles by simple tandem reactions, with no loss of enantioselectivity.
    Grupo de investigación: Organometàl.lics i Catàlisi Homogènia
    Áreas temáticas: Chemistry Química Química
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 1867-3880
    Identificador del autor: n/a; n/a; 0000-0002-2419-0705; 0000-0002-2352-8508; 0000-0002-8450-0656
    Fecha de alta del registro: 2017-02-22
    Página final: 4107
    Volumen de revista: 7
    Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion
    Enlace a la fuente original: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cctc.201500873
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI del artículo: 10.1002/cctc.201500873
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2015
    Página inicial: 4091
    Tipo de publicación: Post-print
  • Palabras clave:

    Catalitzadors de pal·ladi
    Catàlisi asimètrica
    Lligands
    Allylic compounds
    DFT calculations
    allylic substitution
    palladium
    Chemistry
    Química
    Química
    1867-3880
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