Financial support was provided by the National Institute of General Medical Sciences (GM65407). We also thank Merck Research Laboratories, GlaxoSmithKline, Amgen, and Eli Lilly for unrestricted support. We thank Professor Andre Charette (Montreal) for helpful discussions.
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Communication
Stereoselective Lewis Acid Mediated [1,3] Ring Contraction of 2,5-Dihydrooxepins as a Route to Polysubstituted Cyclopentenes†
Article first published online: 21 APR 2005
DOI: 10.1002/anie.200500088
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Nasveschuk, C. G. and Rovis, T. (2005), Stereoselective Lewis Acid Mediated [1,3] Ring Contraction of 2,5-Dihydrooxepins as a Route to Polysubstituted Cyclopentenes. Angew. Chem. Int. Ed., 44: 3264–3267. doi: 10.1002/anie.200500088
- †
Publication History
- Issue published online: 17 MAY 2005
- Article first published online: 21 APR 2005
- Manuscript Received: 11 JAN 2005
Keywords:
- cyclopentenes;
- diastereoselectivity;
- Lewis acids;
- rearrangement;
- ring contraction
A room-temperature diastereoselective [1,3] rearrangement results from treatment of 2,5-dihydrooxepins with EtAlCl2 (see scheme). A modular synthesis of dihydrooxepins allows substituents to be incorporated at any position on the ring, which means that various polysubstituted cyclopentenes can be prepared through this Lewis acid mediated [1,3] ring contraction.