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  • Title: A new silicon lewis acid for highly enantioselective mannich reactions of aliphatic ketone-derived hydrazones.
    Author: Notte GT, Leighton JL.
    Journal: J Am Chem Soc; 2008 May 28; 130(21):6676-7. PubMed ID: 18444641.
    Abstract:
    The first general method for the highly enantioselective Mannich reaction of aliphatic ketimines is reported. A new, second generation chiral silane Lewis acid has been developed that promotes the reaction between ketone-derived hydrazones and silyl ketene acetals, providing the beta,beta-disubstituted beta-amino esters with good enantioselectivity even for the hydrazone derived from 2-butanone (methyl vs ethyl, 91% ee). Several examples are provided, including a reaction with a substituted (propanoate-derived) silyl ketene acetal.
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