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Full Paper
Epoxidation of 4-Alkylidenecyclopentenones: A Route to the 1-Oxaspiro[2.4]hept-6-en-5-one Framework
Article first published online: 30 OCT 2012
DOI: 10.1002/ejoc.201201030
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Ahmar, M., Thomé, S. and Cazes, B. (2012), Epoxidation of 4-Alkylidenecyclopentenones: A Route to the 1-Oxaspiro[2.4]hept-6-en-5-one Framework. Eur. J. Org. Chem., 2012: 7093–7105. doi: 10.1002/ejoc.201201030
Publication History
- Issue published online: 4 DEC 2012
- Article first published online: 30 OCT 2012
- Manuscript Received: 1 AUG 2012
Keywords:
- Synthetic methods;
- Epoxidation;
- Spiro compounds
Abstract
Thanks to their lack of polarity, the exocyclic double bonds of 4-alkylidenecyclopentenones 4 are selectively epoxidized by MCPBA to give spiroepoxycyclopentenones 7, which feature the nonclassical 1-oxaspiro[2.4]hept-6-en-5-one framework. Under acidic conditions, compounds 7 undergo ring-opening to afford 4-hydroxy-4-(1-hydroxyalkyl)cyclopentenones 10.