Articles producció científica> Química Física i Inorgànica

Computationally guided design of a readily assembled phosphite-thioether ligand for a broad range of pd-catalyzed asymmetric allylic substitutions

  • Dades identificatives

    Identificador: imarina:4123832
    Autors:
    Biosca MMargalef JCaldentey XBesora MRodríguez-Escrich CSaltó JCambeiro XMaseras FPàmies ODiéguez MPericàs M
    Resum:
    © 2018 American Chemical Society. A modular approach employing indene as common starting material, has enabled the straightforward preparation in three reaction steps of P-thioether ligands for the Pd-catalyzed asymmetric allylic substitution. The analysis of a starting library of P-thioether ligands based on rational design and theoretical calculations has led to the discovery of an optimized anthracenethiol derivative with excellent behavior in the reaction of choice. Improving most approaches reported to date, this ligand presents a broad substrate and nucleophile scope. Excellent enantioselectivities have been achieved for a range of linear and cyclic allylic substrates using a large number of C-, N-, and O-nucleophiles (40 compounds in total). The species responsible for the catalytic activity have been further investigated by NMR in order to clearly establish the origin of the enantioselectivity. The resulting products have been derivatized by means of ring-closing metathesis or Pauson-Khand reactions to further prove the synthetic versatility of the methodology for preparing enantiopure complex structures.
  • Altres:

    Autor segons l'article: Biosca M; Margalef J; Caldentey X; Besora M; Rodríguez-Escrich C; Saltó J; Cambeiro X; Maseras F; Pàmies O; Diéguez M; Pericàs M
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Besora Bonet, Maria / Biosca Brull, Maria / Diéguez Fernández, Montserrat / Margalef Pallarès, Jèssica / Pamies Ollé, Oscar / Saltó De La Torre, Joan
    Paraules clau: Hashtag Etiqueta «#» @uroweb @residentesaeu @infoAeu
    Resum: © 2018 American Chemical Society. A modular approach employing indene as common starting material, has enabled the straightforward preparation in three reaction steps of P-thioether ligands for the Pd-catalyzed asymmetric allylic substitution. The analysis of a starting library of P-thioether ligands based on rational design and theoretical calculations has led to the discovery of an optimized anthracenethiol derivative with excellent behavior in the reaction of choice. Improving most approaches reported to date, this ligand presents a broad substrate and nucleophile scope. Excellent enantioselectivities have been achieved for a range of linear and cyclic allylic substrates using a large number of C-, N-, and O-nucleophiles (40 compounds in total). The species responsible for the catalytic activity have been further investigated by NMR in order to clearly establish the origin of the enantioselectivity. The resulting products have been derivatized by means of ring-closing metathesis or Pauson-Khand reactions to further prove the synthetic versatility of the methodology for preparing enantiopure complex structures.
    Àrees temàtiques: Química Materiais Interdisciplinar General chemistry Engenharias ii Ciências agrárias i Chemistry, physical Chemistry (miscellaneous) Chemistry (all) Catalysis Astronomia / física
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 21555435
    Adreça de correu electrònic de l'autor: maria.biosca@urv.cat maria.besora@urv.cat joan.salto@estudiants.urv.cat joan.salto@estudiants.urv.cat oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Identificador de l'autor: 0000-0002-9116-6318 0000-0002-6656-5827 0000-0003-4846-8473 0000-0003-4846-8473 0000-0002-2352-8508 0000-0002-8450-0656
    Pàgina final: 3601
    Data d'alta del registre: 2024-09-07
    Volum de revista: 8
    Versió de l'article dipositat: info:eu-repo/semantics/submittedVersion
    Enllaç font original: https://pubs.acs.org/doi/10.1021/acscatal.7b04192
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Acs Catalysis. 8 (4): 3587-3601
    Referència de l'ítem segons les normes APA: Biosca M; Margalef J; Caldentey X; Besora M; Rodríguez-Escrich C; Saltó J; Cambeiro X; Maseras F; Pàmies O; Diéguez M; Pericàs M (2018). Computationally guided design of a readily assembled phosphite-thioether ligand for a broad range of pd-catalyzed asymmetric allylic substitutions. Acs Catalysis, 8(4), 3587-3601. DOI: 10.1021/acscatal.7b04192
    DOI de l'article: 10.1021/acscatal.7b04192
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2018
    Pàgina inicial: 3587
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Catalysis,Chemistry (Miscellaneous),Chemistry, Physical
    Química
    Materiais
    Interdisciplinar
    General chemistry
    Engenharias ii
    Ciências agrárias i
    Chemistry, physical
    Chemistry (miscellaneous)
    Chemistry (all)
    Catalysis
    Astronomia / física
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