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The Evolution of Phosphite-Oxazoline Ligands for the Pd-Allylic Substitution and Their Application in Building Chiral Molecules

  • Dades identificatives

    Identificador: imarina:9325995
    Autors:
    Biosca, MTarr, DPàmies, ODiéguez, M
    Resum:
    Pd-catalyzed asymmetric allylic substitution (AAS) is a highly effective method for producing chiral molecules with alkene-substituted frameworks which can be further derivatized. However, its stereochemical outcome is affected by the steric requirements of the substrate and only a narrow set of nucleophiles yield excellent enantioselectivities. In this regard, phosphite-oxazolines have emerged as strong candidates to be privileged ligands for this process, providing results that surpass most of the previously published studies. They have provided high enantiocontrol when used in the Pd-AAS of several hindered and unhindered substrates, using a wide range of C-, O-, and N-nucleophiles. In this concept, we review and discuss the current progress made in the design of tailor-made phosphite-oxazoline ligand libraries for the Pd-AAS of a broad range of substrates and nucleophiles and its application in the construction of chiral complex molecules.
  • Altres:

    Autor segons l'article: Biosca, M; Tarr, D; Pàmies, O; Diéguez, M
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Biosca Brull, Maria / Diéguez Fernández, Montserrat / Pamies Ollé, Oscar / Tarr González, Daniel James
    Codi de projecte: Grant agreement No. 945413
    Paraules clau: Pauson-khand reaction Palladium P,n-ligands Kinetic resolution Cyclization Asymmetric allylic substitution sesquiterpene pauson-khand reaction palladium p n-ligands functionalization esters cyclization catalysis carbonates asymmetric induction alkylation alcohols
    Resum: Pd-catalyzed asymmetric allylic substitution (AAS) is a highly effective method for producing chiral molecules with alkene-substituted frameworks which can be further derivatized. However, its stereochemical outcome is affected by the steric requirements of the substrate and only a narrow set of nucleophiles yield excellent enantioselectivities. In this regard, phosphite-oxazolines have emerged as strong candidates to be privileged ligands for this process, providing results that surpass most of the previously published studies. They have provided high enantiocontrol when used in the Pd-AAS of several hindered and unhindered substrates, using a wide range of C-, O-, and N-nucleophiles. In this concept, we review and discuss the current progress made in the design of tailor-made phosphite-oxazoline ligand libraries for the Pd-AAS of a broad range of substrates and nucleophiles and its application in the construction of chiral complex molecules.
    Àrees temàtiques: Química Physical and theoretical chemistry Organic chemistry Materiais Interdisciplinar Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências agrárias i Ciência de alimentos Chemistry, organic Biotecnología Biodiversidade Astronomia / física
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: danieljames.tarr@urv.cat maria.biosca@urv.cat oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Identificador de l'autor: 0000-0002-9116-6318 0000-0002-2352-8508 0000-0002-8450-0656
    Data d'alta del registre: 2024-08-03
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.202300429
    Programa de finançament: Marie Sklodowska-Curie Actions – European Union’s Horizon 2020 research and innovation programme
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: European Journal Of Organic Chemistry. 26 (36):
    Referència de l'ítem segons les normes APA: Biosca, M; Tarr, D; Pàmies, O; Diéguez, M (2023). The Evolution of Phosphite-Oxazoline Ligands for the Pd-Allylic Substitution and Their Application in Building Chiral Molecules. European Journal Of Organic Chemistry, 26(36), -. DOI: 10.1002/ejoc.202300429
    Acrònim: MFP-Plus
    DOI de l'article: 10.1002/ejoc.202300429
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2023
    Acció del programa de finançament: Martí i Franquès COFUND Doctoral Programme
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Chemistry, Organic,Organic Chemistry,Physical and Theoretical Chemistry
    Pauson-khand reaction
    Palladium
    P,n-ligands
    Kinetic resolution
    Cyclization
    Asymmetric allylic substitution
    sesquiterpene
    pauson-khand reaction
    palladium
    p
    n-ligands
    functionalization
    esters
    cyclization
    catalysis
    carbonates
    asymmetric induction
    alkylation
    alcohols
    Química
    Physical and theoretical chemistry
    Organic chemistry
    Materiais
    Interdisciplinar
    Farmacia
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências agrárias i
    Ciência de alimentos
    Chemistry, organic
    Biotecnología
    Biodiversidade
    Astronomia / física
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