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Synfacts 2009(2): 0177-0177  
DOI: 10.1055/s-0028-1087633
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Asymmetric Reductive Mannich Reaction

Contributor(s): Mark Lautens, Praew Thansandote
Y. Du, L.-W. Xu, Y. Shimizu, K. Oisaki, M. Kanai*, M. Shibasaki*
The University of Tokyo, Japan
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Publikationsdatum:
22. Januar 2009 (online)

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Significance

A copper(I)-catalyzed asymmetric reductive Mannich reaction of ketimines is described. The scope is broad for a variety of substituted ketimines and α,β-unsaturated esters. An enantioselective variant is shown using a chiral phosphine ligand. For the enantioselective version, silanes are more successful reducing agents than pinacolboranes. The diphenylphosphinoyl group on the ketimines can be removed under acidic conditions.