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Rare Gold-Catalyzed 4-exo-dig Cyclization for Ring Expansion of Propargylic Aziridines toward Stereoselective (Z)-Alkylidene Azetidines, via Diborylalkyl Homopropargyl Amines

  • Dades identificatives

    Identificador: imarina:9380067
    Handle: https://hdl.handle.net/20.500.11797/imarina9380067
    Autors:
    Salvado, OriolPerez-Ruiz, JorgeMesas, AlbaDiaz-Requejo, M MarRerez, Pedro JFernandez, Elena
    Resum:
    We report an uncommon 4-exo-dig cyclization of N-tosyl homopropargyl amines, catalyzed by [AuCl(PEt3)]/AgOTf, to prepare stereoselective (Z)-2-alkylidene-1-tosylazetidine compounds. The reaction outcome contrasts with the gold-catalyzed cyclization of N-tosyl homopropargyl amines containing a methyl group at the propargylic position that provides substituted 2,3-dihydropyrroles via a 5-endo-dig mechanism. The access to N-tosyl homopropargyl amines is possible by the regioselective nucleophilic attack of alpha-diboryl alkylidene lithium salts to propargylic aziridines.

  • Altres:

    Autor segons l'article: Salvado, Oriol; Perez-Ruiz, Jorge; Mesas, Alba; Diaz-Requejo, M Mar; Rerez, Pedro J; Fernandez, Elena
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Fernández Gutiérrez, Maria Elena / Fernández López, Elena / Salvadó Ruiz, Oriol
    Paraules clau: Epoxides Rule
    Resum: We report an uncommon 4-exo-dig cyclization of N-tosyl homopropargyl amines, catalyzed by [AuCl(PEt3)]/AgOTf, to prepare stereoselective (Z)-2-alkylidene-1-tosylazetidine compounds. The reaction outcome contrasts with the gold-catalyzed cyclization of N-tosyl homopropargyl amines containing a methyl group at the propargylic position that provides substituted 2,3-dihydropyrroles via a 5-endo-dig mechanism. The access to N-tosyl homopropargyl amines is possible by the regioselective nucleophilic attack of alpha-diboryl alkylidene lithium salts to propargylic aziridines.
    Àrees temàtiques: Biochemistry Biodiversidade Biotecnología Chemistry, organic Ciências agrárias i Ciências biológicas i Ciências biológicas ii Farmacia General medicine Interdisciplinar Materiais Medicina i Medicina ii Organic chemistry Physical and theoretical chemistry Química
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: mariaelena.fernandez@urv.cat oriol.salvado@alumni.urv.cat
    Identificador de l'autor: 0000-0001-9025-1791
    Data d'alta del registre: 2025-02-18
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Referència a l'article segons font original: Organic Letters. 26 (36): 7535-7540
    Referència de l'ítem segons les normes APA: Salvado, Oriol; Perez-Ruiz, Jorge; Mesas, Alba; Diaz-Requejo, M Mar; Rerez, Pedro J; Fernandez, Elena (2024). Rare Gold-Catalyzed 4-exo-dig Cyclization for Ring Expansion of Propargylic Aziridines toward Stereoselective (Z)-Alkylidene Azetidines, via Diborylalkyl Homopropargyl Amines. Organic Letters, 26(36), 7535-7540. DOI: 10.1021/acs.orglett.4c02415
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2024
    Tipus de publicació: Journal Publications

  • Paraules clau:

    Biochemistry,Chemistry, Organic,Organic Chemistry,Physical and Theoretical Chemistry
    Epoxides
    Rule
    Biochemistry
    Biodiversidade
    Biotecnología
    Chemistry, organic
    Ciências agrárias i
    Ciências biológicas i
    Ciências biológicas ii
    Farmacia
    General medicine
    Interdisciplinar
    Materiais
    Medicina i
    Medicina ii
    Organic chemistry
    Physical and theoretical chemistry
    Química

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