氨基醇砌块用于螺／环丙环类手性化合物的合成

Application of Amino Alcohol as Chiral Building Block in Synthesis of Spiro-Cyclopropane Derivatives Containing Multiple Stereogenic Centers

手性氨基醇砌块3与5-(l-孟氧基)-3-溴-2(5H)-呋喃酮手性合成子4通过串联的不对称双Michael加成/分子内亲核取代反应,得到了具有四个新的手性中心的氨基醇手性砌块/螺环/环丙烷类化合物7(44%～57%,de≥98%).通过元素分析,[α]20D,UV,IR,1HNMR,13C NMR,MS确认了它们的化学结构.本工作可以为含有某些活性官能团的多手性中心的复杂结构化合物提供新的合成策略.

The unusual, functionalized spiro-cyclopropane derivatives 7 containing four stereogenic centers were obtained in good yields with de greater than or equal to 98% via tandem double Michael addition/internal nucleophilic substitution of the chiral synthon, 5-l-menthyloxy-3-bromo-2-(5H)-furanone (4), with amino alcohol as chiral building block 3 under mild conditions. The novel chiral compounds 7 were identified on the basis of their analytical data and spectroscopic data, such as UV, IR, H-1 NMR, C-13 NMR, MS and elementary analysis. This result can provide important synthetic strategy in synthesis of some complex molecules containing spiro-cyclopropane skeleton with multiple chiral centers.