We thank Prof. Gerry Pattenden of the University of Nottingham, and Prof. Pierre De Clercq from Ghent University, for their interest and advice in this study. We also thank undergraduates Maria Gomez Rodriguez, Nick Van Hulle, and Ilaria Villa for preparing and performing initial studies with dienes 16, 18, and 21. The Fund for Scientific Research Flanders (FWO) and the Research Board of Ghent University are acknowledged for financial support. Computational resources and services used in this work were provided by Ghent University.
Scope and Mechanism of the (4+3) Cycloaddition Reaction of Furfuryl Cations†
Article first published online: 9 SEP 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 50, pages 11990–11993, December 9, 2011
How to Cite
Winne, J. M., Catak, S., Waroquier, M. and Van Speybroeck, V. (2011), Scope and Mechanism of the (4+3) Cycloaddition Reaction of Furfuryl Cations. Angew. Chem. Int. Ed., 50: 11990–11993. doi: 10.1002/anie.201104930
- Issue published online: 7 DEC 2011
- Article first published online: 9 SEP 2011
- Manuscript Received: 14 JUL 2011
- Fund for Scientific Research Flanders (FWO)
- Research Board of Ghent University
- DFT calculations;
- fused-ring systems
It all adds up: Furfuryl alcohols are revealed as direct reaction partners for a wide range of conjugated dienes in a (4+3) cycloaddition motif (see scheme). This novel Lewis acid promoted process gives straightforward access to various polycyclic skeletons containing a seven-membered ring. A plausible cationic stepwise mechanism was confirmed by DFT calculations.