Synfacts 2009(6): 0636-0636  
DOI: 10.1055/s-0029-1216716
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Addition of Allyl Cyanide to Ketones

Contributor(s): Hisashi Yamamoto, Joshua P. Abell
R. Yazaki, N. Kumagai*, M. Shibasaki*
The University of Tokyo, Japan
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25. Mai 2009 (online)


Ketones are inherently less reactive to nucleophilic addition than their aldehydes counterparts. Moreover, the enantioselective addition of various nucleophile further compounds the possible problems encountered due to the steric similarities in ketones relative to that of aldehydes. In this report, the authors have shown an efficient copper-catalyzed reaction that provides useful tertiary alcohols with a Z-configured unsaturated nitrile.