Organometal additions to α-iminoesters: N-alkylationvia umpolung

Abstract

α-Iminoesters are useful precursors to substituted α-amino acid derivatives and are utilized in a number of organic transformations. As a consequence of the adjacent ester functionality, these imines are more reactive relative to other types of imines. While a significant body of work has focused on nucleophilic additions to the imine carbon (C-alkylation), a second pathway that involves nucleophilic reaction at the nitrogen (N-alkylation) is much less explored. This tutorial review highlights work that has exploited this unusual α-iminoester reactivity mode.