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