Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

Ming Chang P. Yeh, Chi Fen Jou, Wei Tzou Yeh, Da Yu Chiu, N. Ravi Kumar Reddy

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18 Citations (Scopus)

Abstract

Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene- and -1,3,5-triene-tethered nitrile oxides gave tricyclic isoxazolines as a single stereoisomer in most cases. The relative stereochemistry of tricycle-fused isoxazolines resulting from 1,3-dipolar cycloaddition of cyclo-1,3-diene- tethered nitrile oxides is cis-cis, whereas from cyclohepta-1,3,5-triene- tethered nitrile oxides the cis-trans isomer predominates.

Original languageEnglish
Pages (from-to)493-500
Number of pages8
JournalTetrahedron
Volume61
Issue number2
DOIs
Publication statusPublished - 2005 Jan 10

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Keywords

  • Aldoximes
  • Cyclohepta-1,3,5-trienes
  • Cyclohexa- and cyclohepta-1,3-dienes
  • Isoxazolines

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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