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

  • Datos identificativos

    Identificador: imarina:3658373
    Autores:
    Margalef J, Pàmies O, Diéguez M
    Resumen:
    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.
  • Otros:

    Autor según el artículo: Margalef J, Pàmies O, Diéguez M
    Departamento: Química Física i Inorgànica Química Física i Inorgànica
    e-ISSN: 1521-3765
    Autor/es de la URV: Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
    Palabras clave: Rhodium Phosphite-thioether ligands Iridium Cyclic ¿-enamides Cyclic ?-enamides Asymmetric hydrogenation phosphite-thioether ligands iridium cyclic ?-enamides asymmetric hydrogenation
    Resumen: 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.
    Grupo de investigación: Organometàl·lics i Catàlisi Homogènia
    Áreas temáticas: 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
    Direcció de correo del autor: oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Identificador del autor: 0000-0002-2352-8508 0000-0002-8450-0656
    Página final: 822
    Fecha de alta del registro: 2024-09-07
    Volumen de revista: 23
    Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion
    Enlace a la fuente original: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201604483
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Chemistry-A European Journal. 23 (4): 813-822
    Referencia de l'ítem segons les normes 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
    DOI del artículo: 10.1002/chem.201604483
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2017
    Página inicial: 813
    Tipo de publicación: Journal Publications
  • Palabras clave:

    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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