【摘要】 手性元5-(R)-(1R,2S,5R)-孟氧基-3-溴-2(5H)-呋喃酮(3)与氮亲核试剂伯胺(4),通过串联的不对称Michael加成/分子内亲核取代反应得到了具有两个新的手性中心的1R,5S-6-烷基-6-氮杂-2R-孟氧基-3-氧杂-4-氧代二环[3,1,0]己烷(5a～5d),产率41%～51%,e.e.≥98%.后者经LiAlH4还原得到N-烷基-2,3-双(羟甲基)氮杂环丙烷(6a～6d),产率66%～91%.化合物5和6通过元素分析,IR,1HNMR,13CNMR,MS以及X射线晶体分析,测定了它们的化学结构及立体化学构型.本文为N-烷基氮杂环丙烷类化合物的合成提供了一种有效途径.更多还原

【Abstract】 The chiral 1R,5S-6-alkyl-6-aza-2R-menthoxy-3-oxa-4-oxobicyclo[3,1,0]hexane (5a～5d) con-taining two stereogenic centers were obtained in 41%～51% yields with e.e.≥98% via the tandem asym-metric Michael addition and internal nucleophilic substitution reaction of the chiron 3 with the primary amine 4 as a nucleophile. After the effective reduction of compounds 5 by LiAlH4 in THF, the target mole-cules, meso-N-alkyl-2,3-bis(hydroxymethyl)aziridines (6a～6d) were obtained in 66%～91% yields. The chemical structures of 5 and 6 were readily confirmed by analytical and spectroscopic data. The proposed structures of optically active compounds were consistent with the stereochemistry and configuration of their molecules further confirmed by the X-ray crystallography of 5a and 6c. These results could provide a new synthetic route to the functionalized optically active aziridine derivatives.更多还原