摘要
研究了手性元 5 -( R) -( l-氧基 ) -2 ( 5 H ) -呋喃酮与取代苯甲醛肟以次氯酸钙作为氧化剂进行的区域选择性原位 1 ,3 -偶极环加成反应 ,同步生成两个新的手性中心 ,得到了一系列光学纯丁内酯并 [3 ,4-d]-3 -取代基 -异唑啉类化合物 ;应用波谱学手段及 X射线单晶衍射法确证了产物的绝对构型 ,并对产物的核磁共振氢谱规律性加以总结 .
The in situ regioselective 1,3-dipolar cycloaddition of substituted benzaldoxime to 5-(R)-(l-menthyloxy)-2(5H)-furanone using calcium hypochlorite as the oxidant was investigated. Several substituted butyrolacto[3,4-d]isoxazoline compounds containing two novel stereogenic chiral centers were obtained. The structures of the target compounds have been established via the FAB-HRMS, NMR data(involved 1D NOESY) and X-ray diffraction analysis. The characteristic chemical shifts of the γ-lactone ring protons in 1H NMR were also discussed and the configurations of substituted phenyl furoisoxazolines, the adducts of benzonitrile oxide to 5-(R)-(l-menthyloxy)-2(5H)-furanone, could be determined unambiguously by analyzing the 1H NMR data.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
2003年第11期2000-2004,共5页
Chemical Journal of Chinese Universities
