Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 24, Pages 7982-7988Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201300019
Keywords
gold; heterocycles; homogeneous catalysis; multicomponent reactions; oxazoles
Categories
Funding
- Lund University Faculty of Science
- Royal Physiographical Society in Lund
- Swedish Research Council
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Multicomponent reactions are attractive for assembling functionalized heterocyclic compounds. To this end, an efficient gold-catalyzed three-component domino reaction to form oxazoles directly from imines, alkynes, and acid chlorides is presented. The reaction proceeds in a single synthetic step by using a gold(III)-N,N-ethylenebis(salicylimine) (salen) catalyst to give trisubstituted oxazoles in up to 96% yield. The substrate scope, a mechanistic study exploring the role of the gold catalyst, and the synthetic applications of the oxazole products are discussed.
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