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 2008(8): 0845-0845
DOI: 10.1055/s-2008-1078557
DOI: 10.1055/s-2008-1078557
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium-Catalyzed Asymmetric Wagner-Meerwein Shift of Allenylcyclobutanols
B. M. Trost*, J. Xia
Stanford University, USA
Further Information
Publication History
Publication Date:
23 July 2008 (online)
Significance
The authors demonstrate the first asymmetric Wagner-Meerwein shift of allenylcyclobutanol with palladium catalysts by applying hydropalladation of allenes. This method provides a good way to synthesize highly substituted chiral cyclopentanones with an a-chiral O-tertiary center. They showed a further application of this method by utilizing cyclopentanone products with an ester side chain in a Claisen condensation to produce 5,5-cis and 5,6-cis bicyclic compounds.