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Enantioselective Synthesis of Sterically Hindered Tertiary α-Aryl Oxindoles via Palladium-Catalyzed Decarboxylative Protonation. An Experimental and Theoretical Mechanistic Investigation

  • Dades identificatives

    Identificador: imarina:4123847
    Handle: https://hdl.handle.net/20.500.11797/imarina4123847
    Autors:
    Biosca MJackson MMagre MPàmies ONorrby PDiéguez MGuiry P
    Resum:
    © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim We have developed the first catalytic asymmetric preparation of sterically hindered tertiary α-aryl oxindoles via enantioselective palladium-catalyzed decarboxylative protonation of the corresponding α-aryl-β-amido allyl esters. The reaction occurs under very mild conditions and in short reaction times, providing excellent yields and promising enantioselectivities (ee's up to 78%). We have also performed an experimental investigation of the reaction mechanism and employed theoretical calculations to understand the nature of the enantioselectivity-determining step. (Figure presented.).

  • Altres:

    Autor segons l'article: Biosca M; Jackson M; Magre M; Pàmies O; Norrby P; Diéguez M; Guiry P
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Biosca Brull, Maria / Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
    Paraules clau: Α-aryl oxindoles Palladium Mechanisitic investigations Enantioselective catalysis Decarboxylative protonation ?-aryl oxindoles
    Resum: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim We have developed the first catalytic asymmetric preparation of sterically hindered tertiary α-aryl oxindoles via enantioselective palladium-catalyzed decarboxylative protonation of the corresponding α-aryl-β-amido allyl esters. The reaction occurs under very mild conditions and in short reaction times, providing excellent yields and promising enantioselectivities (ee's up to 78%). We have also performed an experimental investigation of the reaction mechanism and employed theoretical calculations to understand the nature of the enantioselectivity-determining step. (Figure presented.).
    Àrees temàtiques: Química Organic chemistry Materiais Engenharias iv Engenharias ii Ciências biológicas ii Ciência de alimentos Chemistry, organic Chemistry, applied Catalysis Biodiversidade Astronomia / física
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 1615-4150
    Adreça de correu electrònic de l'autor: 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
    Pàgina final: 3137
    Data d'alta del registre: 2024-09-07
    Volum de revista: 360
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Advanced Synthesis & Catalysis. 360 (16): 3124-3137
    Referència de l'ítem segons les normes APA: Biosca M; Jackson M; Magre M; Pàmies O; Norrby P; Diéguez M; Guiry P (2018). Enantioselective Synthesis of Sterically Hindered Tertiary α-Aryl Oxindoles via Palladium-Catalyzed Decarboxylative Protonation. An Experimental and Theoretical Mechanistic Investigation. Advanced Synthesis & Catalysis, 360(16), 3124-3137. DOI: 10.1002/adsc.201800507
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2018
    Pàgina inicial: 3124
    Tipus de publicació: Journal Publications

  • Paraules clau:

    Catalysis,Chemistry, Applied,Chemistry, Organic,Organic Chemistry
    Α-aryl oxindoles
    Palladium
    Mechanisitic investigations
    Enantioselective catalysis
    Decarboxylative protonation
    ?-aryl oxindoles
    Química
    Organic chemistry
    Materiais
    Engenharias iv
    Engenharias ii
    Ciências biológicas ii
    Ciência de alimentos
    Chemistry, organic
    Chemistry, applied
    Catalysis
    Biodiversidade
    Astronomia / física

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