螺氮杂环丙烷氧化吲哚的不对称合成研究  

Studies on the asymmetric synthesis of spiroaziridine oxindoles

作　　者：郭娇美 靳少静 董华绘 王琪琳[1] 卜站伟[1] 

机构地区：[1]阻燃与功能材料河南省工程实验室河南大学化学化工学院,河南开封475004

出　　处：《化学研究》2016年第6期729-732,共4页Chemical Research

基　　金：国家自然科学基金(U1504206)

摘　　要：螺环氧化吲哚和氮杂环丙烷都是非常重要的活性骨架,以3-烯氧化吲哚和双保护的羟胺为起始原料,基于Michael加成-取代串联反应,实现了螺氮杂环丙烷氧化吲哚的不对称合成.通过对一系列手性催化剂、反应温度等的筛选,最终确定了奎宁和辛克宁为最优催化剂,分别以28%和34%的对映选择性得到目标产物,其结构经过1~H NMR、^(13)C NMR和HRMS确定.Spirooxindoles and aziridines are important biologically active scaffolds.In this paper,asymmetric Michael addition/substitution sequence of methyleneindolinones with N-tosyloxycarbamates for the construction of chiral spiroaziridine oxindole was realized.After a systematic screening of chiral catalysts and reaction temperatures,finally,quinine and cinchonine were proved to be the best catalysts,and the corresponding product was obtained in 28% and34% enantioselectivies,respectively.The structure of the product was determined by ~1H NMR,^（13）C NMR and HRMS.

关 键 词：氮杂环丙烷 螺环氧化吲哚 不对称合成 对映选择性 

分 类 号：O621.3[理学—有机化学]