Plancq B, Justafort LC, Lafantaisie M, Ollevier T * Université Laval, Québec, Canada
Gallium(III) Triflate Catalyzed Diastereoselective Mukaiyama Aldol Reaction by Using Low Catalyst Loadings.
Eur. J. Org. Chem. 2013; 6525-6529
Key words
gallium - Mukaiyama aldol reaction - Lewis acids
Significance
The authors report a mild method for the diastereoselective Mukaiyama aldol reaction. The process is catalyzed by gallium(III) triflate yielding to the corresponding β-hydroxy ketones in up to 92% yield.
Comment
The developed method is an efficient aldol reaction under mild conditions with a very low catalyst loading of gallium(III) triflate (0.01–1.0 mol%). This is the first example of a metal triflate acting as a safe and stable slow-releasing source of triflic acid in the Mukaiyama aldol reaction. Gallium(III) triflate is a stable, easy-to-handle white solid.