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Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

  • Dades identificatives

    Identificador: imarina:9187291
    Autors:
    Pàmies OMargalef JCañellas SJames JJudge EGuiry PJMoberg CBäckvall JEPfaltz APericàs MADiéguez M
    Resum:
    This Review compiles the evolution, mechanistic understanding, and more recent advances in enantioselective Pd-catalyzed allylic substitution and decarboxylative and oxidative allylic substitutions. For each reaction, the catalytic data, as well as examples of their application to the synthesis of more complex molecules, are collected. Sections in which we discuss key mechanistic aspects for high selectivity and a comparison with other metals (with advantages and disadvantages) are also included. For Pd-catalyzed asymmetric allylic substitution, the catalytic data are grouped according to the type of nucleophile employed. Because of the prominent position of the use of stabilized carbon nucleophiles and heteronucleophiles, many chiral ligands have been developed. To better compare the results, they are presented grouped by ligand types. Pd-catalyzed asymmetric decarboxylative reactions are mainly promoted by PHOX or Trost ligands, which justifies organizing this section in chronological order. For asymmetric oxidative allylic substitution the results are grouped according to the type of nucleophile used.
  • Altres:

    Autor segons l'article: Pàmies O; Margalef J; Cañellas S; James J; Judge E; Guiry PJ; Moberg C; Bäckvall JE; Pfaltz A; Pericàs MA; Diéguez M
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
    Paraules clau: Transition-metal Phosphite-oxazoline ligands Linked bis(oxazoline) ligands Kinetic resolution Force-field parameters Chiral diaminophosphine oxide Carbon quaternary stereocenters C-h oxidation Asymmetric 3+2 cycloaddition Alkylation total-synthesis
    Resum: This Review compiles the evolution, mechanistic understanding, and more recent advances in enantioselective Pd-catalyzed allylic substitution and decarboxylative and oxidative allylic substitutions. For each reaction, the catalytic data, as well as examples of their application to the synthesis of more complex molecules, are collected. Sections in which we discuss key mechanistic aspects for high selectivity and a comparison with other metals (with advantages and disadvantages) are also included. For Pd-catalyzed asymmetric allylic substitution, the catalytic data are grouped according to the type of nucleophile employed. Because of the prominent position of the use of stabilized carbon nucleophiles and heteronucleophiles, many chiral ligands have been developed. To better compare the results, they are presented grouped by ligand types. Pd-catalyzed asymmetric decarboxylative reactions are mainly promoted by PHOX or Trost ligands, which justifies organizing this section in chronological order. For asymmetric oxidative allylic substitution the results are grouped according to the type of nucleophile used.
    Àrees temàtiques: Química Materiais General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas ii Ciências biológicas i Ciência de alimentos Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Biotecnología
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Identificador de l'autor: 0000-0002-2352-8508 0000-0002-8450-0656
    Data d'alta del registre: 2024-07-27
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://pubs.acs.org/doi/10.1021/acs.chemrev.0c00736
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Chemical Reviews. 121 (8): 4373-4505
    Referència de l'ítem segons les normes APA: Pàmies O; Margalef J; Cañellas S; James J; Judge E; Guiry PJ; Moberg C; Bäckvall JE; Pfaltz A; Pericàs MA; Diéguez M (2021). Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications. Chemical Reviews, 121(8), 4373-4505. DOI: 10.1021/acs.chemrev.0c00736
    DOI de l'article: 10.1021/acs.chemrev.0c00736
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2021
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Transition-metal
    Phosphite-oxazoline ligands
    Linked bis(oxazoline) ligands
    Kinetic resolution
    Force-field parameters
    Chiral diaminophosphine oxide
    Carbon quaternary stereocenters
    C-h oxidation
    Asymmetric 3+2 cycloaddition
    Alkylation total-synthesis
    Química
    Materiais
    General medicine
    General chemistry
    Farmacia
    Engenharias iii
    Engenharias ii
    Ciências biológicas ii
    Ciências biológicas i
    Ciência de alimentos
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Biotecnología
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