Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2006(8): 0815-0815
DOI: 10.1055/s-2006-942018
DOI: 10.1055/s-2006-942018
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
(E)- or (Z)-α-Fluoroenones via Kinetically Controlled Negishi Coupling
G. Dutheuil, C. Paturel, X. Lei, S. Couve-Bonnaire, X. Pannecoucke*
Insa de Rouen, Mont-Saint-Aignan, France
Further Information
Publication History
Publication Date:
21 July 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200608/lookinside/thumbnails/10.1055-s-2006-942018-1.jpg)
Significance
The authors describe the synthesis of either (E)- or (Z)-α-fluoroenones through kinetic control. Formation of α-alkoxyvinyl zinc chlorides and subsequent coupling with bromofluoro olefins affords isomerically enriched bromofluoro olefins. The E isomer reacts under Negishi coupling conditions providing high purity of the (Z)-bromofluoroalkene. The product arising from Negishi coupling with the E isomer can be hydrolyzed to the ketone. The (Z)-bromofluoroalkene can then be coupled to give the opposite isomer generated from the kinetic reaction, enabling access to both isomers.