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  • Title: Direct asymmetric alpha-amination of cyclic ketones catalyzed by siloxyproline.
    Author: Hayashi Y, Aratake S, Imai Y, Hibino K, Chen QY, Yamaguchi J, Uchimaru T.
    Journal: Chem Asian J; 2008 Feb 01; 3(2):225-32. PubMed ID: 18165948.
    Abstract:
    trans-tert-Butyldimethylsiloxy-L-proline displays greater catalytic activity and affords higher enantioselectivity than the parent proline in the alpha-amination reaction of carbonyl compounds with azodicarboxylate. A quantum mechanical calculation reveals the structure of the transition state. In the presence of a catalytic amount of siloxyproline and water (3-9 equiv), alpha-amino carbonyl derivatives, which are important synthetic intermediates, are obtained in good yield and with excellent enantioselectivity.
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