Organometal additions to alpha-iminoesters: N-alkylation via umpolung.
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.
Dickstein
Joshua S
JS
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, PA 19104, USA.
Kozlowski
Marisa C
MC
D000478:Alkylation; D001895:Boron / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry
D004952:Esters; D007097:Imines; D009942:Organometallic Compounds; D003300:Copper; D014025:Titanium; D009584:Nitrogen; D001895:Boron