This project was supported by the Deutsche Forschungsgemeinschaft (DFG) and the Fonds der Chemischen Industrie (FCI). We thank Olaf Ackermann for assistance with HPLC. We thank Prof. Thorsten Bach and his group for helpful discussions and generous support.
Catalyzed Tandem Reaction of 3-Silyloxy-1,5-enynes Consisting of Cyclization and Pinacol Rearrangement†
Article first published online: 20 FEB 2007
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 46, Issue 13, pages 2310–2313, March 19, 2007
How to Cite
Kirsch, Stefan F., Binder, Jörg T., Crone, B., Duschek, A., Haug, Timm T., Liébert, C. and Menz, H. (2007), Catalyzed Tandem Reaction of 3-Silyloxy-1,5-enynes Consisting of Cyclization and Pinacol Rearrangement. Angew. Chem. Int. Ed., 46: 2310–2313. doi: 10.1002/anie.200604544
- Issue published online: 9 MAR 2007
- Article first published online: 20 FEB 2007
- Manuscript Received: 6 NOV 2006
- Deutsche Forschungsgemeinschaft (DFG)
- Fonds der Chemischen Industrie (FCI)
- domino reactions;
- homogeneous catalysis;
Au-spicious! Under silver-free conditions, simple 3-silyloxy-1,5-enynes were converted into complex cyclopentenes by a gold(I)-catalyzed sequence that likely proceeds through a carbocyclization followed by a pinacol rearrangement. For the final demetalation step, isopropyl alcohol and N-iodosuccinimide are effectively utilized, and the resulting products are set up for a wealth of further reactions.