A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides

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3 Scopus citations

Abstract

The 1,3-dipolar cycloaddition of keto- and aldonitrones with N-arylitaconimides proceeds regioselectively giving only 5-spiroisoxazolidines. In the case of aldonitrones the reaction proceeds with high diastereoselectivity. A range of the obtained adducts were subjected to reductive cleavage of the N–O bond using zinc powder in acetic acid to give the corresponding spirolactones and 1,3-amino alcohols.

Original languageEnglish
Article number151063
JournalTetrahedron Letters
Volume60
Issue number39
Early online date21 Aug 2019
DOIs
StatePublished - 2019

Scopus subject areas

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

Keywords

  • Cycloaddition
  • Itaconimides
  • Nitrones
  • Reduction
  • DIASTEREOSELECTIVITY
  • REGIOSELECTIVITY
  • PHENYLNITRONES
  • INHIBITION
  • NITRILE OXIDES
  • 1,3-DIPOLAR CYCLOADDITION
  • BIOLOGICAL EVALUATION
  • LACTAMS
  • SPIRO-ISOXAZOLIDINE DERIVATIVES
  • ALKALOIDS

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