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Synfacts 2008(4): 0378-0378  
DOI: 10.1055/s-2008-1042876
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Mukaiyama Aldol Reaction Catalyzed by Bismuth

Contributor(s): Hisashi Yamamoto, Joshua P. Abell
T. Ollevier*, J.-E. Bouchard, V. Desyroy
Université Laval, Canada
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

Bismuth triflate is shown to catalyze the vinylogous Mukaiyama aldol reaction with 2-(trimethylsilyloxy)furans. Attractive features include mild reaction conditions, low cost and low catalyst loading, along with air and moisture tolerance. Only a small amount of byproducts are formed during the reaction. Furthermore, bismuth is known to be non-toxic.