Wang Y, Chackalamannil S, Aubé J
Department of Medicinal Chemistry, University of Kansas, Lawrence 66045-2506, USA.
J Org Chem. 2000 Aug 25;65(17):5120-6. doi: 10.1021/jo991928g.
A set of conformationally biased imines derived from substituted cyclohexanones and benzylamine or diphenylmethylamine, respectively, were oxidized to the corresponding oxaziridines. The structures of the oxaziridines were determined via NMR comparison of two series of differently N-substituted oxaziridines. Thus, those compounds having an axially disposed nitrogen substituent displayed an upfield-shifted axial proton in a 1,3-relationship to the oxaziridine nitrogen in the N-diphenylmethyl series relative to the N-benzyl compounds. Analysis of the products obtained from these reactions suggests that (1) adjacent hydroxyl groups favor syn oxidant addition and (2) imines containing adjacent methoxy groups preferentially undergo attack anti to the resident alkoxy substituent.
分别由取代环己酮与苄胺或二苯甲基胺衍生得到的一组构象偏向性亚胺被氧化为相应的氮杂环丙烷。通过对两个不同N-取代氮杂环丙烷系列进行核磁共振比较来确定氮杂环丙烷的结构。因此，在N-二苯甲基系列中，相对于N-苄基化合物，那些具有轴向排列的氮取代基的化合物在与氮杂环丙烷氮呈1,3-关系的轴向质子处显示出高场位移。对这些反应所得产物的分析表明：(1) 相邻的羟基有利于氧化剂的顺式加成；(2) 含有相邻甲氧基的亚胺优先受到与驻留烷氧基取代基呈反式的攻击。
