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Synfacts 2009(1): 0062-0062
DOI: 10.1055/s-0028-1087399
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
R. Yazaki, T. Nitabaru, N. Kumagai*, M. Shibasaki*
The University of Tokyo, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. Dezember 2008 (online)
![](https://www.thieme-connect.de/media/synfacts/200901/lookinside/thumbnails/10.1055-s-0028-1087399-1.jpg)
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.