Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3

Yuse Kuriyama, Yusuke Sasano, Yoshihiko Hoshino, Shun ichiro Uesugi, Aoto Yamaichi, Yoshiharu Iwabuchi

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1 Citation (Scopus)

Abstract

Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.

Original languageEnglish
Pages (from-to)1961-1965
Number of pages5
JournalChemistry - A European Journal
Volume27
Issue number6
DOIs
Publication statusPublished - 2021 Jan 26

Keywords

  • amines
  • chemoselectivity
  • cyclization
  • regioselectivity
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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