Articles producció científica> Química Física i Inorgànica

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

  • Identification data

    Identifier: imarina:9380067
    Authors:
    Salvado, OriolPerez-Ruiz, JorgeMesas, AlbaDiaz-Requejo, M MarRerez, Pedro JFernandez, Elena
    Abstract:
    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.
  • Others:

    Author, as appears in the article.: Salvado, Oriol; Perez-Ruiz, Jorge; Mesas, Alba; Diaz-Requejo, M Mar; Rerez, Pedro J; Fernandez, Elena
    Department: Química Física i Inorgànica
    URV's Author/s: Fernández Gutiérrez, Maria Elena / Fernández López, Elena / Salvadó Ruiz, Oriol
    Keywords: Epoxides Rule
    Abstract: 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.
    Thematic Areas: 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
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: mariaelena.fernandez@urv.cat oriol.salvado@alumni.urv.cat
    Author identifier: 0000-0001-9025-1791
    Record's date: 2025-02-18
    Paper version: info:eu-repo/semantics/publishedVersion
    Paper original source: Organic Letters. 26 (36): 7535-7540
    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
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2024
    Publication Type: Journal Publications
  • Keywords:

    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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