Articles producció científica> Química Física i Inorgànica

Modular hydroxyamide and thioamide pyranoside-based ligand library from the sugar pool: new class of ligands for asymmetric transfer hydrogenation of ketones

  • Dades identificatives

    Identificador: PC:687
    Autors:
    Coll, M.Pàmies, O.Diéguez, M.
    Resum:
    10.1002/adsc.201301112
  • Altres:

    Autor segons l'article: Coll, M. Pàmies, O. Diéguez, M.
    Departament: Química Física i Inorgànica
    Paraules clau: Hydrogenation
    Resum: A large library of pyranoside‐based hydroxyamide and thioamide ligands has been synthesized for asymmetric transfer hydrogenation in an attempt to expand the scope of the substrates to cover a broader range of challenging heteroaromatic and aryl/fluoroalkyl ketones. These ligands have the advantage that they are prepared from commercial D‐glucose, D‐glucosamine and α‐amino acids, inexpensive natural chiral feedstocks. By carefully selecting the ligand components (substituents/configurations at the amide/thioamide moiety, the position of amide/thioamide group and the configuration at C‐2), we found that pyranoside‐based thioamide ligands provided excellent enantioselectivities (in the best cases, ees of >99% were achieved) in a broad range of ketones, including the less studied heteroaromatics and challenging aryl/fluoroalkyls. Note that both enantiomers of the reduction products can be obtained with excellent enantioselectivities by simply changing the absolute configuration of the thioamide substituent.
    Àrees temàtiques: Catalysis
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 1615-4150
    Pàgina final: 2302
    Volum de revista: 356
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201301112/abstract
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1002/adsc.201301112
    Entitat: Universitat Rovira i Virgili.
    Any de publicació de la revista: 2014
    Pàgina inicial: 2293
  • Paraules clau:

    Asymmetric catalysis
    Hydrogenation
    Catalysis
    1615-4150
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