科研成果转化为有机化学教学实验之探索.

This work provides a research-oriented comprehensive organic chemistry teaching experiment converted from a mature scientific research achievement in desymmetrization of meso and other prochiral compounds. The naturally-occurring cinchona alkaloids quinine mediated organocatalytic enantioselective methanolysis of meso-cyclic anhydride was utilizedas a tool for preparation of the corresponding chiral hemiester, which is the key intermediate of ( + )-biotin, and the products were characterized by IR , NMR spectroscopy and specific rotation. Finally, the method of crystallization resolution of diastereoisomers was usedto recycle organocatalyst quinine. Through the experiment students not only consolidate the basic principles of asymmetric synthesis and chemical resolution, but also have abetter understanding of instrument working principle and improve the actual operation skills of the rotary evaporator, thin layer chromatography, infrared spectrometer and nuclear magnetic resonance instrument. In a word, the systematic experimental procedure can help students to consolidate the comprehensive ability including the relevant synthetic strategy of organic chemistry, synthetic chemistry experiment skill and spectra analysis. Moreover, the recovery process of organocatalyst creates a favorable teaching environment to set up the concept of “green chemistry” for undergraduates. [ABSTRACT FROM AUTHOR]