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  • Title: Chiral scandium catalysts for enantioselective Michael reactions of beta-ketoesters.
    Author: Ogawa C, Kizu K, Shimizu H, Takeuchi M, Kobayashi S.
    Journal: Chem Asian J; 2006 Jul 17; 1(1-2):121-4. PubMed ID: 17441046.
    Abstract:
    A highly enantioselective Michael reaction of beta-ketoesters with alpha,beta-unsaturated ketones promoted by a chiral scandium catalyst has been developed. In the presence of Sc(OTf)3 and (S,S)-6,6'-bis(1-hydroxy-2,2'-dimethylpropyl)-2,2'-bipyridine, the desired Michael reactions proceeded smoothly in dichloroethane at 40 degrees C to afford the corresponding adducts in good to high yields with excellent enantioselectivities in most cases. It was found in this reaction that a lower concentration of the reaction mixture was key to attaining high enantioselectivities.
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