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Synfacts 2006(4): 0354-0354  
DOI: 10.1055/s-2006-932050
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Asymmetric Domino Reductive Aldol Reactions

Contributor(s): Mark Lautens, Y. Eric Fang
J. Deschamp, O. Chuzel, J. Hannedouche, O. Riant*
Université Catholique de Louvain, Belgium
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

The authors report a Cu(I)-catalyzed asymmetric reductive aldol reaction of a ­methyl ketone and methyl acrylate using a catalytic amount of Cu(I), taniaphos, and PhSiH3 as a hydride source. Under these optimal conditions, a threo-β-hydroxy-α,β-dimethylester was obtained in good to excellent enantioselectivity and good diastereoselectivity. Various acetophenones as well as some hetereoaryl methyl ketones were tolerated in this transformation.