Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 8, Pages 2382-2388Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103080
Keywords
aldol reaction; cycloisomerization; cyclopenta[b]furans; domino reactions; electrocyclic reactions
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Funding
- Universidad Nacional de Rosario
- Fundacion Josefina Prats
- CONICET
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A new cascade pathway viable for Knoevenagel chemistry that involves the coupling between 1,3-dicarbonyl systems and alpha,beta,gamma,delta-unsaturated aldehydes has been developed. The process comprises the combination of a classic aldol-type condensation and a rare spontaneous metal-free cycloisomerization, representing a convergent and innovative approach for the stereoselective synthesis of cyclopenta[b]furan-type derivatives. The scope and limitations with respect to both reaction partners and mechanistic features were investigated. Meaningfully, our study provides valuable guidance concerning the structural and electronic effects controlling the reactivity of conjugated polyene carbonyl systems.
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