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Updated: Jul 5, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Organometal additions to alpha-iminoesters: N-alkylation via umpolung
Joshua S Dickstein1, Marisa C Kozlowski
1Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, PA 19104, USA.
Abstract:
Alpha-iminoesters are useful precursors to substituted alpha-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 alpha-iminoester reactivity mode.
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