Dickstein Joshua S, Kozlowski Marisa C
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, PA 19104, USA.
Chem Soc Rev. 2008 Jun;37(6):1166-73. doi: 10.1039/b709139g. Epub 2008 Apr 1.
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.
α-亚氨基酯是制备取代α-氨基酸衍生物的有用前体，并用于多种有机转化反应中。由于相邻的酯官能团，这些亚胺相对于其他类型的亚胺更具反应活性。虽然大量的研究工作集中在对亚胺碳的亲核加成反应（C-烷基化）上，但涉及氮原子亲核反应（N-烷基化）的第二条途径却很少被探索。本综述重点介绍了利用这种不寻常的α-亚氨基酯反应模式的研究工作。
