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

  • Identification data

    Identifier: imarina:4123842
    Authors:
    Borràs CElías-Rodríguez PCarmona ARobina IPàmies ODiéguez M
    Abstract:
    © 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.
  • Others:

    Author, as appears in the article.: Borràs C; Elías-Rodríguez P; Carmona A; Robina I; Pàmies O; Diéguez M
    Department: Química Física i Inorgànica
    URV's Author/s: BORRÀS NOGUERA, CARLOTA / Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
    Keywords: @infoAeu @residentesaeu @uroweb Etiqueta «#» Hashtag
    Abstract: © 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.
    Thematic Areas: 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
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0276-7333
    Author's mail: oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Author identifier: 0000-0002-2352-8508 0000-0002-8450-0656
    Last page: 1694
    Record's date: 2024-09-07
    Journal volume: 37
    Papper version: info:eu-repo/semantics/submittedVersion
    Link to the original source: https://pubs.acs.org/doi/10.1021/acs.organomet.8b00140
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Organometallics. 37 (11): 1682-1694
    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
    Article's DOI: 10.1021/acs.organomet.8b00140
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2018
    First page: 1682
    Publication Type: Journal Publications
  • Keywords:

    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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