A facile synthesis of bridged-tricyclic skeletons via intramolecular Diels-Alder reaction of cyclic 1,3-dienes containing an α,β- unsaturated ester

Ming Chang P. Yeh, Wen Cheng Tsao, Ching Jing Liu

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Abstract

Intramolecular Diels-Alder reaction (IMDA) precursors are easily available starting from addition of ester functionalized zinc-copper reagents to cyclohexadienyl- and cycloheptadienylirontricarbonyl cation salts. The resulting cyclic 1,3-dienes containing an α,β-unsaturated ester functionality underwent smoothly IMDA reaction to afford bridged tricyclic compounds. Bridged heterotricyclic skeletons were also available via IMDA reaction of cyclic 1,3-dienes bearing an imine or aldehyde functionality.

Original languageEnglish
Pages (from-to)383-387
Number of pages5
JournalJournal of the Chinese Chemical Society
Volume52
Issue number2
DOIs
Publication statusPublished - 2005 Jan 1

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Keywords

  • Bridged-tricyclic compound
  • Cyclic 1,3-diene
  • Intramolecular Diels-Alder reaction

ASJC Scopus subject areas

  • Chemistry(all)

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