Articles producció científica> Química Física i Inorgànica

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

  • Identification data

    Identifier: PC:2568
    Authors:
    Maria BioscaMarc MagrePer-Ola NorrbyOscar PàmiesMontserrat Diéguez
    Abstract:
    Filiació URV: SIInclòs a la memòria: SI
  • Others:

    Author, as appears in the article.: Maria Biosca; Marc Magre; Per-Ola Norrby; Oscar Pàmies; Montserrat Diéguez
    Department: Química Física i Inorgànica
    URV's Author/s: BIOSCA BRULL, MARIA; Marc Magre; Per-Ola Norrby; PAMIES OLLÉ, OSCAR; DIÉGUEZ FERNÁNDEZ, MONTSERRAT
    Keywords: DFT calculations allylic substitution palladium
    Abstract: 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.
    Research group: Organometàl.lics i Catàlisi Homogènia
    Thematic Areas: Chemistry Química Química
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 1867-3880
    Author identifier: n/a; n/a; 0000-0002-2419-0705; 0000-0002-2352-8508; 0000-0002-8450-0656
    Record's date: 2017-02-22
    Last page: 4107
    Journal volume: 7
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cctc.201500873
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1002/cctc.201500873
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2015
    First page: 4091
    Publication Type: Post-print
  • Keywords:

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