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BORON TRIFLUORIDE-MEDIATED SYNTHESIS OF N-ARYL-SUBSTITUTED PYRROLIDINES FROM TETRAHYDROFURAN AND AMINES
Abstract
Boron trifluoride-mediated transformation of tetrahydrofuran to corresponding N-aryl-substituted pyrrolidines is conducted under mild
reaction conditions, providing a practical synthetic method with reasonable yields. Computational studies confirmed the reaction
mechanism involving a fast Lewis acid-assisted ring-opening step, followed by the 7-membered intermediate formation and a ringclosing
process as the rate-determining step.
reaction conditions, providing a practical synthetic method with reasonable yields. Computational studies confirmed the reaction
mechanism involving a fast Lewis acid-assisted ring-opening step, followed by the 7-membered intermediate formation and a ringclosing
process as the rate-determining step.
Keywords
N-aryl-substituted pyrrolidines, cyclic ether, Lewis acid, tetrahydrofuran activation, ring opening.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv