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Synfacts 2011(8): 0866-0866  
DOI: 10.1055/s-0030-1260732
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Hydrocyanation of α,β-Unsaturated Ketones

Contributor(s): Mark Lautens, Patrick T. Franke
N. Kurono, N. Nii, Y. Sakaguchi, M. Uemura, T. Ohkuma*
Hokkaido University, Sapporo, Japan
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Publikationsdatum:
20. Juli 2011 (online)

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Significance

An efficient enantioselective conjugate addition of HCN to α,β-unsaturated ketones catalyzed by the combined system of [Ru{(S)-­phgly}2{(S)-binap}] and PhOLi has been reported. Generally, the hydrocyanation afforded β-cyano ketones in high yield and excellent enantioselectivity. It is noteworthy that no corresponding 1,2-adduct was detected and that the reaction was conducted with a substrate-to-catalyst molar ratio in the range of 200:1 to 1000:1.