Synfacts 2007(6): 0610-0610  
DOI: 10.1055/s-2007-968497
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

GaCl3-Catalyzed Stereoselective Synthesis of E-α,β-Unsaturated Ketones

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
J. S. Yadav*, B. V. S. Reddy, M. K. Gupta, U. Dash, S. K. Pandey
Indian Institute of Chemical Technology, Hyderabad, India
Further Information

Publication History

Publication Date:
22 May 2007 (online)

Significance

The authors have developed a very mild and highly stereoselective synthesis of α,β-unsaturated ketones. Gallium chloride was the new catalyst used for this reaction in 10 mol% loading. GaCl3 has a very unusual reactivity, and a variety of new reactions have been reported recently (for a short review see: R. Amemiya, M. Yamaguchi, Eur. J. Org. Chem. 2005, 5145-5150). A variety of aryl substrates added to ynones giving the products in high yield and selectivity. All reactions are finished in less than one hour and yields are generally very high.