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

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...

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Detalles Bibliográficos
Autores: Salvadó, Oriol, Pérez Ruíz, Jorge, Mesas, Alba, Díaz Requejo, María Mar, Pérez Romero, Pedro José, Fernández Gutiérrez, Elena
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universidad de Huelva (UHU)
Repositorio:Arias Montano. Repositorio Institucional de la Universidad de Huelva
Idioma:inglés
OAI Identifier:oai:ariasmontano.uhu.es:10272/24247
Acceso en línea:https://hdl.handle.net/10272/24247
Access Level:acceso abierto
Palabra clave:Amines
Aziridines
Cyclization
Lithium
Reagents
23 Química
Descripción
Sumario: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 α-diboryl alkylidene lithium salts to propargylic aziridines

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