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Synfacts 2011(8): 0869-0869  
DOI: 10.1055/s-0030-1260731
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed 1,4-Addition of Organo-boronates to Alkylidene Cyanoacetates

Contributor(s): Mark Lautens, Patrick T. Franke
K. Takatsu, R. Shintani, T. Hayashi*
Kyoto University, Japan
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Publikationsdatum:
20. Juli 2011 (online)

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Significance

The authors report on a mild ­copper/N-heterocyclic carbene (NHC) catalyzed 1,4-addition of organoboronates to alkylidene ­cyanoacetates. Employing a newly synthesized chiral NHC ligand gives access to a broad range of enantiomerically enriched 1,4-adducts. How­ever, it should be mentioned that different activating groups as EWG or CN afforded the corresponding products in lower yields.