We thank Karl Collins for helpful discussions. This work was supported by the Alexander von Humboldt Foundation (Z.S.) and the Deutsche Forschungsgemeinschaft (IRTG Münster-Nagoya). Generous financial support by the European Research Council under the European Community’s Seventh Framework Program (FP7 2007-2013)/ERC Grant agreement no. 25936 is gratefully acknowledged.
Mild Rhodium(III)-Catalyzed Cyclization of Amides with α,β-Unsaturated Aldehydes and Ketones to Azepinones: Application to the Synthesis of the Homoprotoberberine Framework†
Article first published online: 16 APR 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 20, pages 5393–5397, May 10, 2013
How to Cite
Shi, Z., Grohmann, C. and Glorius, F. (2013), Mild Rhodium(III)-Catalyzed Cyclization of Amides with α,β-Unsaturated Aldehydes and Ketones to Azepinones: Application to the Synthesis of the Homoprotoberberine Framework . Angew. Chem. Int. Ed., 52: 5393–5397. doi: 10.1002/anie.201301426
- Issue published online: 3 MAY 2013
- Article first published online: 16 APR 2013
- Manuscript Received: 18 FEB 2013
- Alexander von Humboldt Foundation
- Deutsche Forschungsgemeinschaft
- European Research Council. Grant Number: 25936
- CH activation;
Seven! The title reaction can be described as an intermolecular annulation involving tandem CH activation, cyclization to give the seven-membered ring, and condensation steps. Biologically interesting azepinone derivatives can be prepared in this way. The synthetic potential of this method was demonstrated by the construction of the homoprotoberberine ring system.