摘要
研究了手性试剂 5 (l 孟氧基 ) 3 溴 2 (5H) 呋喃酮 (5a)与中等碳链的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 4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～d .利用旋光、元素分析、UV、IR、1HNMR、13CNMR、MS等进行了结构表征 .
The synthesis of a novel chiral synthon, 5 ( l menthyloxy) 3 bromo 2(5H) furanone (5a), and its application in asymmetric reaction are investigated. The unusual functionalized spiro cyclopropane derivatives containing four stereogenic centers 8a～d are 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 are identified on the basis of their analytical and spectroscopic ([ α ] 20 D,UV, IR, 1 HNMR, 13 CNMR, MS) and X ray crystallographic data.
出处
《北京师范大学学报（自然科学版）》
CAS
CSCD
北大核心
2000年第1期85-88,共4页
Journal of Beijing Normal University(Natural Science)
基金
国家自然科学基金!资助项目 (2 96 72 0 0 4)
关键词
手性合成子
呋喃酮
绝对构型
环内烷类化合物
novel chiral synthon
5 ( l menthyloxy) 3 bromo 2(5H) furanone
absolute configuration
tandem asymmetric Michael reaction and internal nucleophilic substitution
enantiomerically pure spiro cyclopropane derivatives containing multiple
