BORON TRIFLUORIDE-MEDIATED SYNTHESIS OF <i>N</i>-ARYL-SUBSTITUTED PYRROLIDINES FROM TETRAHYDROFURAN AND AMINES

Authors

  • Zhihong Wang State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University

DOI:

https://doi.org/10.1007/4059

Keywords:

N-aryl-substituted pyrrolidines, cyclic ether, Lewis acid, tetrahydrofuran activation, ring opening.

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.

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Published

2018-01-18

Issue

Vol. 53 No. 12 (2017)

Section

Short Communications