Faculty of Pharmaceutical Sciences, Setsunan University , 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
Org Lett. 2014 Apr 18;16(8):2080-3. doi: 10.1021/ol500631j. Epub 2014 Apr 3.
An enantioselective Reformatsky reaction has been developed for the reaction of ethyl dibromofluoroacetate (1) with an imine. This method represents the first ligand-promoted imino-Reformatsky approach to use a halofluoroacetate. The use of an amino alcohol ligand allowed for the preparation of enantioenriched α-bromo-α-fluoro-β-lactams in good yields with enantioselectivities up to 96% ee. This process also provided access to β-lactam rings bearing two stereogenic centers.
发展了一种对映选择性 Reformatsky 反应，用于二溴氟代乙酸乙酯（1）与亚胺的反应。该方法代表了首例使用卤氟代乙酸酯的配体促进亚氨基 Reformatsky 方法。使用氨基醇配体可以以良好的收率和高达 96%ee 的对映选择性制备出对映体富集的α-溴-α-氟-β-内酰胺。该过程还提供了具有两个手性中心的β-内酰胺环的途径。
