Triflic Acid Catalyzed Intermolecular α-Amination of Pterolactams to Give 5-Arylaminopyrrolidinones via N-Acyliminium Species

Gina-Mirabela Dumitriu (1) , Elena Bîcu (1) , Ulku Eryuruk (2) , Dalila Belei (1) , Benoît Rigo (3, 2) , Adam Daïch (4, 5) , Alina Ghinet (3, 1, 2)

1 Alexandru Ioan Cuza University of Iași [Romania]
2 HEI - Hautes Etudes d’Ingénieur [Lille]
3 LIRIC - Lille Inflammation Research International Center - U 995
4 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire
5 INC3M - Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire

A mild and efficient α-aza-amidoalkylation for the synthesis of 5-arylaminopyrrolidinones is presented. The key step of this reaction is the intermolecular interception of an N-acyliminium species, generated under the acidic conditions, with nitrogen nucleophiles such as N-silylamines. © Georg Thieme Verlag Stuttgart New York.

Keywords: N-silylamine; N-acyliminium cation; triflic acid; pterolactam; alkylation

Domains: Chemical Sciences

Gina-Mirabela Dumitriu, Elena Bîcu, Ulku Eryuruk, Dalila Belei, Benoît Rigo, et al.. Triflic Acid Catalyzed Intermolecular α-Amination of Pterolactams to Give 5-Arylaminopyrrolidinones via N-Acyliminium Species. SYNLETT, 2016, 27 (6), pp.934-940. ⟨10.1055/s-0035-1561333⟩. ⟨hal-02413305⟩