A new silicon lewis acid for highly enantioselective mannich reactions of aliphatic ketone-derived hydrazones |
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Authors: | Notte Gregory T Leighton James L |
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Institution: | Department of Chemistry, Columbia University, New York, New York 10027, USA. |
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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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