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Short Communication
Construction of Fused Medium-Ring Carbocycles by Catalytic Generation and Rearrangement of Oxonium Ylides
Article first published online: 21 NOV 2005
DOI: 10.1002/ejoc.200500830
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Clark, J. S., Walls, S. B., Wilson, C., East, S. P. and Drysdale, M. J. (2006), Construction of Fused Medium-Ring Carbocycles by Catalytic Generation and Rearrangement of Oxonium Ylides. Eur. J. Org. Chem., 2006: 323–327. doi: 10.1002/ejoc.200500830
Publication History
- Issue published online: 2 JAN 2006
- Article first published online: 21 NOV 2005
- Manuscript Received: 24 OCT 2005
Keywords:
- Carbenoids;
- Ylides;
- Rearrangements;
- Medium-sized rings;
- Carbocycles
Abstract
Fused carbocyclic systems containing seven- and eight-membered rings can be constructed from allylic ethers in a stereoselective manner by tandem carbenoid generation, ylide formation and [2,3] rearrangement. Exceptionally high yields are obtained in cases where the substrate possesses favourable relative stereochemistry. The dienes resulting from [2,3] rearrangement of gem-divinyl ylides undergo Diels–Alder cycloaddition with reactive dienophiles at room temperature. Ylide formation, rearrangement and cycloaddition can be performed in a one-pot process to generate complex tetracyclic systems in a highly stereoselective manner. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)