This work is supported by NSERC (Canada), Merck Frosst (IRC), and the University of Toronto. K.M.G. thanks the Deutsche Forschungsgemeinschaft (DFG) for a postdoctoral scholarship. We also thank Brian Mariampillai, Dr. Michael Langer, and Dr. David Hulcoop for helpful discussions, and Dr. A. Lough for X-ray analysis.
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
The Norbornene Shuttle: Multicomponent Domino Synthesis of Tetrasubstituted Helical Alkenes through Multiple C![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
H Functionalization†
Article first published online: 14 JAN 2009
DOI: 10.1002/anie.200805512
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Gericke, Kersten M., Chai, David I., Bieler, N. and Lautens, M. (2009), The Norbornene Shuttle: Multicomponent Domino Synthesis of Tetrasubstituted Helical Alkenes through Multiple CH Functionalization. Angew. Chem. Int. Ed., 48: 1447–1451. doi: 10.1002/anie.200805512
- †
Publication History
- Issue published online: 30 JAN 2009
- Article first published online: 14 JAN 2009
- Manuscript Received: 11 NOV 2008
Funded by
- NSERC (Canada)
- Merck Frosst
- University of Toronto
- Deutsche Forschungsgemeinschaft (DFG)
Keywords:
- CH activation;
- domino reactions;
- multicomponent reactions;
- palladium;
- strained molecules
Abstract
Shall we dance? Within the proposed mechanism for the palladium-catalyzed title reaction, the strained alkene norbornene (or norbornadiene) enters and exits the catalytic cycle in a catalytic “square dance”, acting as both a promoter and a coupling partner in the formation of four carbon–carbon bonds, two of them by challenging CH activation processes.