L-脯氨酸拆分1,1′-联-2-萘酚的实验设计

Experimental design for chiral resolution of 1,1′-bi-2-naphthols with L-proline

为了将手性化合物的包结拆分法引入有机化学实验教学,设计了有机化学综合实验“L-脯氨酸拆分1,1′-联-2-萘酚”:将L-脯氨酸和外消旋联萘酚研磨后,乙腈回流后析出L-脯氨酸和(S)-BINOL形成的包合物,(R)-BINOL留在溶液中。该综合实验实现了光学纯联萘酚的高效拆分,创新了教学体系。实践表明,该综合实验采用基于非共价键作用的包结拆分法进行手性拆分,激发了学生的学习兴趣;此外,该实验综合性强,有利于学生动手操作能力、分析和解决综合问题能力的培养。

In order to bring the concept of enantioselective inclusion complexation into basic organic chemistry experiment teaching,chiral resolution of 1,1′-bi-2-naphthols with L-proline was designed.An improved method of chiral resolution of rac-BINOLs was developed.Rac-BINOL and L-proline were ground and refluxed in acetonitrile,and the resulting white precipitate was recrystallized in ethanol to improve the optical purity of(S')-BINOL and shorten the reaction time.The improved method could furnish BINOL enantiomer with>99%ee efficiently.This designed experiment is comprehensive,it not only stimulates students’interest in learning with novel teaching models,but also helps them develop their ability to analyze and solve practical problems.