Articles producció científica> Química Física i Inorgànica

Amino-P Ligands from Iminosugars: New Readily Available and Modular Ligands for Enantioselective Pd-Catalyzed Allylic Substitutions

  • Datos identificativos

    Identificador: imarina:4123842
    Handle: http://hdl.handle.net/20.500.11797/imarina4123842
  • Autores:

    Borràs C
    Elías-Rodríguez P
    Carmona A
    Robina I
    Pàmies O
    Diéguez M
  • Otros:

    Autor según el artículo: Borràs C; Elías-Rodríguez P; Carmona A; Robina I; Pàmies O; Diéguez M
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: BORRÀS NOGUERA, CARLOTA / Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
    Palabras clave: @infoAeu @residentesaeu @uroweb Etiqueta «#» Hashtag
    Resumen: © 2018 American Chemical Society. The construction of a novel class of amino-phosphite/phosphinite/phosphine ligands containing a protected pyrrolidine-3,4-diol moiety is presented. These ligands are obtained from readily available sugars. They thus contain the advantages of carbohydrates in terms of selection of the stereogenic carbons, polyfunctional groups able to modulate the electronic and steric properties, and the general good stability of carbohydrate derivatives. They constitute a novel class of P,N-ligands that have been used in the enantioselective allylic substitutions of acyclic and cyclic substrates with varied electronic and steric requirements, using different C- and N-nucleophiles, with high enantioselectivities. Among the three groups of P,N-ligands (amino-P; P = phosphite, phosphinite, and phosphine groups) the new amino-phosphite ligands give the widest substrate and nucleophile scope, including the more challenging hindered linear and cyclic substrates. In particular, for carbohydrate-derived amino-phosphite ligands and linear substrates, high enantioselectivity in the reactions requires an R configuration of the binaphthyl moiety. However, for cyclic substrates both product enantiomers can be reached by setting out the chirality of the binaphthyl phosphite moiety. A detailed investigation of the appropriate Pd intermediates is also presented.
    Áreas temáticas: Química Physical and theoretical chemistry Organic chemistry Materiais Inorganic chemistry Engenharias ii Ciências biológicas ii Ciências agrárias i Chemistry, organic Chemistry, inorganic & nuclear Astronomia / física
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0276-7333
    Direcció de correo del autor: montserrat.dieguez@urv.cat oscar.pamies@urv.cat
    Identificador del autor: 0000-0002-8450-0656 0000-0002-2352-8508
    Página final: 1694
    Fecha de alta del registro: 2023-02-18
    Volumen de revista: 37
    Versión del articulo depositado: info:eu-repo/semantics/submittedVersion
    Enlace a la fuente original: https://pubs.acs.org/doi/10.1021/acs.organomet.8b00140
    URL Documento de licencia: http://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Organometallics. 37 (11): 1682-1694
    Referencia de l'ítem segons les normes APA: Borràs C; Elías-Rodríguez P; Carmona A; Robina I; Pàmies O; Diéguez M (2018). Amino-P Ligands from Iminosugars: New Readily Available and Modular Ligands for Enantioselective Pd-Catalyzed Allylic Substitutions. Organometallics, 37(11), 1682-1694. DOI: 10.1021/acs.organomet.8b00140
    DOI del artículo: 10.1021/acs.organomet.8b00140
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2018
    Página inicial: 1682
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Chemistry, Inorganic & Nuclear,Chemistry, Organic,Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry
    Química
    Physical and theoretical chemistry
    Organic chemistry
    Materiais
    Inorganic chemistry
    Engenharias ii
    Ciências biológicas ii
    Ciências agrárias i
    Chemistry, organic
    Chemistry, inorganic & nuclear
    Astronomia / física
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