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Synfacts 2009(1): 0062-0062  
DOI: 10.1055/s-0028-1087399
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Cu/Li-Catalyzed Asymmetric Addition of Allylic Cyanides to Ketoimines

Contributor(s): Mark Lautens, Praew Thansandote
R. Yazaki, T. Nitabaru, N. Kumagai*, M. Shibasaki*
The University of Tokyo, Japan
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

An asymmetric copper-catalyzed addition of allylic cyanides to ketoimines forming quaternary stereocenters is described. Good yields, cis/trans selectivities, and ee values are seen for aromatic, heteroaromatic, and aliphatic keto­imines. Aside from allylcyanide, 3-methylallyl ­cyanide can also be used, although longer reaction times were required. Deprotection of the N-Dpp group can be accomplished under acidic conditions (12 N HCl) to give the corresponding amine salts.