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Full Paper
One-Pot Organocatalytic Tandem Aldol/Polycyclization Reactions between 1,3-Dicarbonyl Compounds and α,β,γ,δ-Unsaturated Aldehydes for the Straightforward Assembly of Cyclopenta[b]furan-Type Derivatives: New Insight into the Knoevenagel Reaction
Article first published online: 16 JAN 2012
DOI: 10.1002/chem.201103080
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Riveira, M. J. and Mischne, M. P. (2012), One-Pot Organocatalytic Tandem Aldol/Polycyclization Reactions between 1,3-Dicarbonyl Compounds and α,β,γ,δ-Unsaturated Aldehydes for the Straightforward Assembly of Cyclopenta[b]furan-Type Derivatives: New Insight into the Knoevenagel Reaction. Chem. Eur. J., 18: 2382–2388. doi: 10.1002/chem.201103080
Publication History
- Issue published online: 10 FEB 2012
- Article first published online: 16 JAN 2012
- Manuscript Received: 1 OCT 2011
Funded by
- Universidad Nacional de Rosario and Fundación Josefina Prats
- CONICET
Keywords:
- aldol reaction;
- cycloisomerization;
- cyclopenta[b]furans;
- domino reactions;
- electrocyclic reactions
Abstract
A new cascade pathway viable for Knoevenagel chemistry that involves the coupling between 1,3-dicarbonyl systems and α,β,γ,δ-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.