Articles producció científica> Química Física i Inorgànica

Phosphite-Thiother Ligands Derived from Carbohydrates allow the Enantioswitchable Hydrogenation of Cyclic ¿-Enamides by using either Rh or Ir Catalysts

  • Identification data

    Identifier: imarina:3658373
    Authors:
    Margalef J, Pàmies O, Diéguez M
    Abstract:
    Phosphite-thioether ligands with a simple modular architecture, derived from inexpensive l-(+)-tartaric acid and d-mannitol, have been for the first time successfully applied (ee values up to 99 %) in the synthesis of 2-aminotetralines and 3-aminochromanes by metal-catalyzed asymmetric hydrogenation of cyclic ¿-enamides. The ligands have the advantages of the robustness of the thioether/phosphite moieties and the extra control provided by the flexibility of the chiral pocket through the presence of a biaryl phosphite group and a modular carbohydrate-derived backbone. Moreover, they are solid and stable to air and they are therefore easy to handle, manipulate, and store. Usefully, both enantiomers of the hydrogenated products were obtained by simply switching from Rh to Ir. Low hydrogen pressure and environmentally friendly propylene carbonate can be used, with no loss of selectivity.
  • Others:

    Author, as appears in the article.: Margalef J, Pàmies O, Diéguez M
    Department: Química Física i Inorgànica Química Física i Inorgànica
    e-ISSN: 1521-3765
    URV's Author/s: Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
    Keywords: Rhodium Phosphite-thioether ligands Iridium Cyclic ¿-enamides Cyclic ?-enamides Asymmetric hydrogenation phosphite-thioether ligands iridium cyclic ?-enamides asymmetric hydrogenation
    Abstract: Phosphite-thioether ligands with a simple modular architecture, derived from inexpensive l-(+)-tartaric acid and d-mannitol, have been for the first time successfully applied (ee values up to 99 %) in the synthesis of 2-aminotetralines and 3-aminochromanes by metal-catalyzed asymmetric hydrogenation of cyclic ¿-enamides. The ligands have the advantages of the robustness of the thioether/phosphite moieties and the extra control provided by the flexibility of the chiral pocket through the presence of a biaryl phosphite group and a modular carbohydrate-derived backbone. Moreover, they are solid and stable to air and they are therefore easy to handle, manipulate, and store. Usefully, both enantiomers of the hydrogenated products were obtained by simply switching from Rh to Ir. Low hydrogen pressure and environmentally friendly propylene carbonate can be used, with no loss of selectivity.
    Research group: Organometàl·lics i Catàlisi Homogènia
    Thematic Areas: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física
    ISSN: 15213765
    Author's mail: oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Author identifier: 0000-0002-2352-8508 0000-0002-8450-0656
    Last page: 822
    Record's date: 2024-09-07
    Journal volume: 23
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201604483
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Chemistry-A European Journal. 23 (4): 813-822
    APA: Margalef J, Pàmies O, Diéguez M (2017). Phosphite-Thiother Ligands Derived from Carbohydrates allow the Enantioswitchable Hydrogenation of Cyclic ¿-Enamides by using either Rh or Ir Catalysts. Chemistry-A European Journal, 23(4), 813-822. DOI: 10.1002/chem.201604483
    Article's DOI: 10.1002/chem.201604483
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2017
    First page: 813
    Publication Type: Journal Publications
  • Keywords:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Organic Chemistry
    Rhodium
    Phosphite-thioether ligands
    Iridium
    Cyclic ¿-enamides
    Cyclic ?-enamides
    Asymmetric hydrogenation
    phosphite-thioether ligands
    iridium
    cyclic ?-enamides
    asymmetric hydrogenation
    Química
    Organic chemistry
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias iii
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Biotecnología
    Biodiversidade
    Astronomia / física
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