Synthesis 2019; 51(24): 4650-4656
DOI: 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
,
,
Departamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Toluca, C.P. 50180, México   Email: mromeroo@uaemex.mx
› Author Affiliations
The Consejo Nacional de Ciencia y Tecnología (National Council of Science and Technology) is gratefully acknowledged for providing an M.Sc. fellowship to Zaira A. Santos (CONACyT 642259).
Further Information

Publication History

Received: 03 July 2019

Accepted after revision: 12 September 2019

Publication Date:
08 October 2019 (online)

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.

Supporting Information

 
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