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Synthesis 2019; 51(24): 4650-4656
DOI: 10.1055/s-0037-1610733
DOI: 10.1055/s-0037-1610733
paper
Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N-Acyliminium Ions
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.
Key words
N-acyliminium ions - organozinc reagents - coupling reactions - 5-allyl-2-pyrrolidinones - azabicyclic systemsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610733.
- Supporting Information
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