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Chemistry of Heterocyclic Compounds

, Volume 53, Issue 12, pp 1365–1368 | Cite as

Boron trifluoride-mediated synthesis of N-aryl-substituted pyrrolidines from tetrahydrofuran and amines

  • Shanshan Hu
  • Yan Huo
  • Zhihong WangEmail author
Article

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.

Keywords

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

Notes

The project is funded by the Natural Science Foundation of Tianjin, China (14JCYBJC19700).

Supplementary material

10593_2018_2220_MOESM1_ESM.pdf (480 kb)
ESM 1 (PDF 479 kb)

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.State Key Laboratory and Institute of Elemento-Organic Chemistry, College of ChemistryNankai UniversityTianjinP. R. China

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