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

Research output: Contribution to journalArticle

3 Citations (Scopus)

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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Esters
Bearings (structural)
Imines
Aldehydes
Cations
Zinc
Copper
Salts

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "A facile synthesis of bridged-tricyclic skeletons via intramolecular Diels-Alder reaction of cyclic 1,3-dienes containing an α,β- unsaturated ester",
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.",
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T1 - A facile synthesis of bridged-tricyclic skeletons via intramolecular Diels-Alder reaction of cyclic 1,3-dienes containing an α,β- unsaturated ester

AU - Yeh, Ming Chang P.

AU - Tsao, Wen Cheng

AU - Liu, Ching Jing

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N2 - 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.

AB - 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.

KW - Bridged-tricyclic compound

KW - Cyclic 1,3-diene

KW - Intramolecular Diels-Alder reaction

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