辛可尼丁催化合成手性3,3’-双取代氧化吲哚的实验设计  

Experimental Design on Synthesis of Chiral 3,3’-disubstituted Oxindole Catalyzed by Cinchonidine

作　　者：白丽娟 周静[1] BAI Li-juan;ZHOU Jing(College of Pharmacy,Chongqing Medical University,Chongqing 400010,China)

机构地区：[1]重庆医科大学药学院

出　　处：《广州化工》2019年第20期137-139,173,共4页GuangZhou Chemical Industry

摘　　要：介绍了辛可尼丁催化3-羧酸酯-2-氧化吲哚与N-苄基马来酰亚胺的不对称Michael加成反应的实验设计.-35℃反应2 h后,柱层析得到手性琥珀酰亚胺取代的3,3'-双取代氧化吲哚,利用手性高效液相色谱测试得到产物的dr值和ee值.本实验将课题组最新科研成果设计成综合性实验,不仅强化训练了学生基本的实验技能和操作,同时让学生接触手性催化、不对称合成等前沿科研方向,拓宽了知识面,培养了学生分析问题、解决问题和科研创新等方面的综合能力.The experimental design on asymmetric Michael addition reaction of 3-carboxylic ester-2-oxindole with N -benzyl maleimide catalyzed by cinchonidine was introduced. After reaction at -35 ℃ for 2 h, chiral succinimide-substituted 3,3 - disubstituted oxindole was obtained by column chromatography. The dr and ee values of the product were determined by chiral high performance liquid chromatography. The latest scientific research results of our research group were designed as a comprehensive experiment. It not only strengthened and trained students basic experimental skills and operations. At the same time, students should be exposed to the frontier research directions of chiral catalysis and asymmetric synthesis. It broadened the scope of knowledge and cultivated students comprehensive abilities in analyzing, solving and innovating scientific research.

关 键 词：不对称催化 辛可尼丁 手性琥珀酰亚胺取代的3 3'-双取代氧化吲哚 不对称MICHAEL加成反应 

分 类 号：O6[理学—化学]