From a spin-off to the advantageous use in Diels-Alder reactions: A combined synthetic, spectroscopic and computational approach to N-(dienyl)acylamines

Dirk G̈rdes, Axel Jacobi Von Wangelin, Stefan Klaus, Helfried Neumann, Dirk Strübing, Sandra Hübner, Haijun Jiao, Wolfgang Baumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

The acid-catalyzed condensation of aldehydes and acetamide has been shown to provide a pool of diverse equilibrating species. For the first time, the synthesis of substituted 1-N-acylamino-1,3-butadienes has been accomplished directly in moderate yields upon telomerization of two molecules of aldehyde with one molecule of carboxamide. Detailed spectroscopic and computational investigations establish the favourable formation of all-trans aminodienes under the reaction conditions. Employment thereof as diene building blocks in Diels-Alder reactions allows for the synthesis of carbocyclic molecules with high stereocontrol.

Original languageEnglish
Pages (from-to)845-851
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number6
DOIs
StatePublished - 21 Mar 2004
Externally publishedYes

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