Abstract The asymmetric alcoholysis of meso-cyclic anhydride under mild reaction conditions was achieved by the synergistic co-catalytic synthesis strategy of “organic acid-organic base”. The enantiomeric excess percentage (ee value) of the chiral half-ester product was determined by HPLC with pre-column derivatization. In this teaching experiment, we have integrated various teaching concepts and methods, such as the development concept of green chemistry and other ideological elements, Schlenk techniques, spray chromogenic technique for thin-layer chromatography, pre-column derivatization, chiral HPLC. Thus, a scientific research experiment involving the synthesis of optically active substances and ee value detection was developed into a micro-scale organic synthesis comprehensive experiment suitable for undergraduate education. In addition, modular split teaching can also be carried out to meet the experimental teaching requirements of different contents.
XIONG Fei, ZHU Yi-Ren, SUN Chen, FANG Rui-Jing, HE Yi-Yang, LI Ye-Ji. Synthesis of Chiral Half-Esters: Micro-Scale Asymmetric Catalytic Organic Synthesis Experiment Teaching[J]. Chinese Journal of Chemical Education, 2024, 45(4): 54-59.
