A facile and efficient synthesis of enyne-reaction precursors by multicomponent reactions

Dirk Strübing, Helfried Neumann, Stefan Klaus, Sandra Hübner, Matthias Beller

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

Using improved reaction protocols for three-component coupling reactions of aldehydes, dienophiles, and amides (AAD-reaction) or anhydrides (ANAD-reaction) or orthoesters (ALAD-reaction), a variety of functionalized hexahydroisoindolo derivatives were synthesized and fully characterized. Condensation of ubiquitous available aldehydes with unsaturated amides or anhydrides or orthoesters and subsequent Diels-Alder reactions with electron deficient dienophiles furnishes endo-selective enyne-reaction precursors in good to excellent yield.

Original languageEnglish
Pages (from-to)11333-11344
Number of pages12
JournalTetrahedron
Volume61
Issue number48
DOIs
StatePublished - 28 Nov 2005
Externally publishedYes

Keywords

  • Aldehydes
  • Diels-Alder reaction
  • Enynes
  • Multicomponent coupling reaction

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