Financial support from the Ministry of Education, Culture, Sports, Science, and Technology of Japan, the Asahi Glass Foundation, and the Okayama Foundation for Science and Technology. S.Y.S. also thanks the Japan Society for the Promotion of Science (JSPS) for a Postdoctoral Research Fellowship
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Communication
Rhenium-Catalyzed Synthesis of Stereodefined Cyclopentenes from β-Ketoesters and Aliphatic Allenes†
Article first published online: 7 NOV 2008
DOI: 10.1002/anie.200803350
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 47, Issue 48, pages 9318–9321, November 17, 2008
Additional Information
How to Cite
Yudha S., S., Kuninobu, Y. and Takai, K. (2008), Rhenium-Catalyzed Synthesis of Stereodefined Cyclopentenes from β-Ketoesters and Aliphatic Allenes. Angew. Chem. Int. Ed., 47: 9318–9321. doi: 10.1002/anie.200803350
- †
Publication History
- Issue published online: 12 NOV 2008
- Article first published online: 7 NOV 2008
- Manuscript Revised: 17 SEP 2008
- Manuscript Received: 10 JUL 2008
Funded by
- Ministry of Education, Culture, Sports, Science, and Technology of Japan
- Asahi Glass Foundation
- Okayama Foundation for Science and Technology
- Japan Society for the Promotion of Science
Keywords:
- allenes;
- cyclopentenes;
- rhenium;
- synthetic methods
Come on allene: Commercially available [Re2(CO)10] as a catalyst provides five-membered carbocycles in moderate to excellent yields with high stereoselectivity (see scheme). The configuration at each of the three sp3 carbon centers of the ring is defined. The reaction proceeds at the β, γ, and adjacent methylene positions of the allene; previously, similar reactions usually occurred at the α, β, and γ positions of the allene.