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Synfacts 2007(11): 1196-1196
DOI: 10.1055/s-2007-991231
DOI: 10.1055/s-2007-991231
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Regioselective Addition of Aldehydes to Enones Catalyzed by a Ruthenium Hydride Complex
T. Fukuyama, T. Doi, S. Minamino, S. Omura, I. Ryu*
Osaka Prefecture University, Japan
Further Information
Publication History
Publication Date:
23 October 2007 (online)
Significance
A novel regioselective addition reaction of aldehydes to enones providing synthetically useful 2-alkyl-substituted 1,3-diketones is reported. Several Ru catalysts were tested in this reaction, where [RuHCl(CO)(PPh3)3] proved to be the most powerful. The presence of PPh3 is necessary for the reaction to proceed. However, the sole presence of PPh3 without the RuH complex is not sufficient. Remote C-C double bonds were found to migrate leading to the formation of the more stable enones which immediately underwent coupling with the respective aldehydes.