Abstract: Resolution is one of the most important methods for the preparation of optically active compounds. Classic physical resolution via crystallization assisted by chiral resolution reagents can usually provide one compound with highly optical purity. As an important asymmetric synthetic technology, kinetic resolution has become a powerful tool for the construction of multifunctional enantioenriched molecules and has been widely used in the synthesis of drugs and natural products. Therefore, we designed a kinetic resolution experiment based on alkene E→Z isomerization catalyzed by a photoexcited chiral copper complex. This experiment involves substrate synthesis, separation and purification, photocatalytic reaction, kinetic resolution curve drawing and condition verification. Many experimental skills are concerned in this experiment, including column chromatography separation, (preparative) thin layer chromatography (TLC), gas chromatography (GC) and chiral high-performance liquid chromatography (HPLC), which can not only exercise students’ comprehensive experimental skills, but also let students feel the advantages of kinetic resolution, photocatalysis and excited transition metal catalysis technologies. The experiment is designed reasonably with strong operability and high safety. It lasts 24 hours in total, including three one-day individual experiments. It is very suitable for the courses of organic chemistry experiment or comprehensive chemistry experiment.

Key words: Kinetic resolution, Photoexcited copper, Transition metal catalysis, Alkene E→Z isomerization