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Synfacts 2014; 10(1): 0065
DOI: 10.1055/s-0033-1340431
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Mukaiyama Aldol Reaction Catalyzed by Gallium(III) Triflate

Contributor(s):
Hisashi Yamamoto
,
Atsuto Izumiseki
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
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Publication History

Publication Date:
13 December 2013 (online)

 
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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.


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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.


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