Journal of the American Chemical Society, Vol.130, No.21, 6676-6676, 2008
A new silicon lewis acid for highly enantioselective Mannich reactions of aliphatic ketone-derived hydrazones
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 ketonederived 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.