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Synfacts 2009(6): 0649-0649  
DOI: 10.1055/s-0029-1216778
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Domino Reductive Aldol Cyclization

Contributor(s): Mark Lautens, Jacki Kitching
J. Deschamp, O. Riant*
Université Catholique de Louvain, Louvain-la-Neuve, Belgium
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

As an extension on previous research involving the copper(I)-catalyzed domino reductive aldol reaction between methyl acrylate, aldehydes and ketones (Angew. Chem. Int. Ed. 2006, 45, 1292; Org. Lett. 2006, 8, 5943), the authors now describe the application of this methodology in the construction of bicyclic compounds. The procedure can be performed on a 10 mmol scale using only 0.5 mol% catalyst and affords the bicyclic products in good diastereo- and enantio-selectivity.