摘要
研究了新的手性试剂,5-(l-氧基)-3-溴-2(5H)-呋喃酮(5a)的合成及其与亲核性醇发生的串联不对称双Michael加成/分子内亲核取代反应。通过此反应,一举生成了四个新的手性中心,得到了一般方法难以合成的含有多个手性中心的丁内酯并螺-环丙烷类化合物8a～8d。详细报道了8a～8d的合成方法以及它们的[α]、IR、UV、~1H NMR、^(13)C NMR、MS、元素分析等结构分析数据。此不对称双Michael加成/分子内亲核取代反应可以为某些新的光学活性螺-环丙烷类化合物以及某些复杂结构的分子提供重要的合成策略。
In this paper, the synthesis of a novel chiral synthon, 5 - ( l - menthyloxy) - 3 - bromo - 2(5H) - fu-ranone (5a) and its application in asymmetric reaction have been investigated. The unusual, functionalized spiro - cyclopropane derivatives containing four stereogenic centers 8a - 8d were obtained in good yields with d. e. (98% via tandem double Michael addition/internal nucleophilic substitution of the novel chiral synthon, 5 - l- menthyloxy - 3 - bromo -2- (5H) - furanone 5a, with oxygen nucleophiles under mild conditions. The structure and configuration were established on the basis of their analytical and spectroscopic ([a]D20, UV, IR,1H NMR,13C NMR,MS) and X- ray crystallo-graphic data.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2000年第1期64-71,共8页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(批准:号29672004)
关键词
呋喃酮
合成
不对称合成
MICHAEL加成反应
novel chiral shnthon, 5 - (l - menthyloxy) - 3 - bromo - 2(5H) - furanone, absolute configuration, tandem asymmetric Michael reaction and internal nucleophilic substitution, enantiomerically pure spiro - cyclopropane derivatives containing mult
