Synthesis, Table of Contents Synthesis 2019; 51(24): 4650-4656DOI: 10.1055/s-0037-1610733 paper © Georg Thieme Verlag Stuttgart · New York Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N-Acyliminium Ions Ivann Zaragoza-Galicia , Zaira A. Santos-Sánchez , Yazmín I. Hidalgo-Mercado , Horacio F. Olivo , Moisés Romero-Ortega ∗ Departamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Toluca, C.P. 50180, México Email: mromeroo@uaemex.mx › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract A coupling reaction between cyclic N-acyliminium ions with organozinc reagents is described. The cyclic N-acyliminium ions, generated in situ from N-substituted-5-hydroxy-2-pyrrolidinones by treatment with boron trifluoride–diethyl ether complex or titanium tetrachloride, are trapped by the organozinc reagent, which is formed from an alkyl bromide in the presence of zinc in the same reaction medium. The N-substituted-5-allyl-2-pyrrolidinones generated using this method serve as versatile intermediates for the synthesis of azabicyclic systems with indolizidine and pyrroloazepinolizidine cores. Key words Key words N-acyliminium ions - organozinc reagents - coupling reactions - 5-allyl-2-pyrrolidinones - azabicyclic systems Full Text References References 1a Gellert E. J. Nat. Prod. 1982; 45: 50 1b Michael JP. Nat. Prod. Rep. 1993; 10: 51 2 Furneaux RH, Gainsford GJ, Mason JM, Tyler PC. Tetrahedron 1994; 50: 2131 ; and references cited therein 3a Lin W.-H, Ye Y, Xu R.-S. J. Nat. Prod. 1992; 55: 571 3b Pilli RA, Ferreira de Oliveira MC. Nat. Prod. Rep. 2000; 17: 117 4 Michael JP. 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