DOI

An effective approach to access functionalized 2H-cyclonona(deca)[d]isoxazoles and 15-oxo-3,10-methanobenzo[b][1]azacyclododecines has been developed by the reaction of N-aryl-C,C-bis(methoxycarbonyl)nitrones with cyclonona(deca)-1,2-dienes in a one-pot fashion. The reaction of N-aryl-C-(phenylcarbamoyl)nitrones with these allenes proceeds strictly regioselectively giving the mixtures of diastereomeric isoxazolidines containing a double bond at the C-4-position of the isoxazolidine ring. The quantum chemical calculations show that the regioselectivity of these reactions is in good agreement with the reactivity indices of the considered compounds.

Original languageEnglish
Pages (from-to)9773-9784
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number44
Early online date26 Oct 2021
DOIs
StatePublished - 28 Nov 2021

    Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

    Research areas

  • 1,3-DIPOLAR CYCLOADDITIONS, ZOSTER VIRUS, ISOXAZOLIDINE, DIASTEREOSELECTIVITY, ANALOGS

ID: 88231747