We thank the National Institutes of Health (GM 28273) and Merck Research Laboratories for generous financial support.
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Stereoselective Synthesis of Highly Substituted Cyclopentenones through [4+1] Annulations of Trialkylsilyl Vinyl Ketenes with α-Benzotriazolyl Organolithium Compounds†
Article first published online: 5 AUG 2005
DOI: 10.1002/anie.200501579
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 44, Issue 36, pages 5867–5870, September 12, 2005
Additional Information
How to Cite
Davie, C. P. and Danheiser, R. L. (2005), Stereoselective Synthesis of Highly Substituted Cyclopentenones through [4+1] Annulations of Trialkylsilyl Vinyl Ketenes with α-Benzotriazolyl Organolithium Compounds. Angew. Chem. Int. Ed., 44: 5867–5870. doi: 10.1002/anie.200501579
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Publication History
- Issue published online: 8 SEP 2005
- Article first published online: 5 AUG 2005
- Manuscript Received: 10 MAY 2005
Keywords:
- annulation;
- azoles;
- cyclopentenones;
- electrocyclic reactions;
- ketenes
Closing the ring: Highly functionalized cyclopentenones are prepared by the reaction of readily available metalated benzotriazole derivatives with trialkylsilyl vinyl ketenes (see scheme; Z=heteroatom substituent). Dienolate intermediates are generated which form the five-membered ring. Most transformations proceed with high stereoselectivity by a mechanism believed to involve stereospecific 4π-electrocyclic ring closure.