利用微波促进氮杂糖硝酮(2)与丙烯酸类衍生物(3)发生1,3-偶极环加成反应,立体选择性地得到了一系列新的含异噁唑烷的氮杂糖衍生物(4),反应效率显著提高,反应时间由95h缩短为5~15min,收率由67%提高到78%~88%.利用NMR和HRMS等方法结合化合物(4d-1)的单晶结构确定了产物的结构和相对构型.
In order to develop an efficient,practical and stereoselective method to access functionalized azasugar derivatives the microwave assisted 1,3-dipolar cycloaddition of azasugar nitrone and acrylates was investigated which afforded a series of novel azasugar derivatives containing an isoxazolindine moiety. The reaction was performed in a sealed microwave reactor at 110 ℃ in the solution of toluene and proceeded efficiently in yields up to 78% —88% within 5—15 min. The structures and configurations of the products were tentatively determined by 1H NMR,13C NMR,2D NMR and HRMS spectral analyses with comparison to the reported X-ray single crystallographic structure of the product 4d-1.