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

  • Identification data

    Identifier: imarina:9187291
    Authors:
    Pamies, OscarMargalef, JessicaCanellas, SantiagoJames, JinjuJudge, EricGuiry, Patrick JMoberg, ChristinaBackvall, Jan-EPfaltz, AndreasPericas, Miquel ADieguez, Montserrat
    Abstract:
    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.
  • Others:

    Author, as appears in the article.: Pamies, Oscar; Margalef, Jessica; Canellas, Santiago; James, Jinju; Judge, Eric; Guiry, Patrick J; Moberg, Christina; Backvall, Jan-E; Pfaltz, Andreas; Pericas, Miquel A; Dieguez, Montserrat
    Department: Química Física i Inorgànica
    URV's Author/s: Diéguez Fernández, Montserrat / MARGALEF LLEBARIA, JOAQUIM / Pamies Ollé, Oscar / Pericàs Brondo, Miquel Àngel
    Keywords: 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
    Abstract: 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.
    Thematic Areas: 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
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: miquelangel.pericas@urv.cat oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Author identifier: 0000-0002-2352-8508 0000-0002-8450-0656
    Record's date: 2024-11-09
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://pubs.acs.org/doi/10.1021/acs.chemrev.0c00736
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Chemical Reviews. 121 (8): 4373-4505
    APA: Pamies, Oscar; Margalef, Jessica; Canellas, Santiago; James, Jinju; Judge, Eric; Guiry, Patrick J; Moberg, Christina; Backvall, Jan-E; Pfaltz, Andreas (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
    Article's DOI: 10.1021/acs.chemrev.0c00736
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2021
    Publication Type: Journal Publications
  • Keywords:

    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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