Articles producció científica> Química Física i Inorgànica

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

  • Identification data

    Identifier: imarina:9325995
  • Authors:

    Biosca, M
    Tarr, D
    Pàmies, O
    Diéguez, M
    European Journal Of Organic Chemistry
    10.1002/ejoc.202300429
    European Journal Of Organic Chemistry. 26 (36):
  • Others:

    Author, as appears in the article.: Biosca, M; Tarr, D; Pàmies, O; Diéguez, M
    Department: Química Física i Inorgànica
    URV's Author/s: Biosca Brull, Maria / Diéguez Fernández, Montserrat / Pamies Ollé, Oscar / Tarr González, Daniel James
    Project code: Grant agreement No. 945413
    Keywords: 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
    Abstract: 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.
    Thematic Areas: 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
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: danieljames.tarr@urv.cat maria.biosca@urv.cat oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Author identifier: 0000-0002-9116-6318 0000-0002-2352-8508 0000-0002-8450-0656
    Record's date: 2024-07-20
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.202300429
    Funding program: Marie Sklodowska-Curie Actions – European Union’s Horizon 2020 research and innovation programme
    Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: European Journal Of Organic Chemistry. 26 (36):
    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
    Acronym: MFP-Plus
    Article's DOI: 10.1002/ejoc.202300429
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2023
    Funding program action: Martí i Franquès COFUND Doctoral Programme
    Publication Type: Journal Publications
  • Keywords:

    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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