Affiliation:
1. Departamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México
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.
Funder
Consejo Nacional de Ciencia y Tecnología
Subject
Organic Chemistry,Catalysis
Cited by
1 articles.
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