Second generation protocol for muticomponent coupling reactions of aldehydes, amides and dienophiles

Stefan Klaus, Sandra Hübner, Helfried Neumann, Dirk Strübing, Axel Jacobi Von Wangelin, Dirk Gördes, Matthias Beller

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

An improved one-pot procedure for the three-component coupling reaction of aldehydes, amides and dienophiles (AAD reaction) has been developed. Compared to known protocols for this type of reaction, the use of aromatic solvents in the presence of dehydrating reagents allows an efficient synthesis of previously not accessible products. Condensation of ubiquitous available aldehydes and amides and subsequent Diels-Alder reactions with dienophiles furnishes endo-selective amino-functionalized hexahydroisoindole-1,3-dione and tetrahydrophthalic acid derivatives in good yield.

Original languageEnglish
Pages (from-to)970-978
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume346
Issue number8
DOIs
StatePublished - Jul 2004
Externally publishedYes

Keywords

  • Aldehydes
  • Aldol reaction
  • Diels-Alder reaction
  • Enamides
  • Multicomponent coupling reactions
  • N-dienyl amides

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