The Synthesis Of Aziridines And Its Ring-opening Reaction By Glucose

This thesis is mainly composed of three parts: First, the synthesis of aziridines by two different methods: one is the addition reaction of nitrene and alkenes, the other is the addition reaction of carbine and imines; second, the regioselective ring opening of aziridines which synthesized in the first step by glucose compounds; third, the synthesis of a chiral complex and two lactone perfumes.In the first part, Chloramine-T was used as the nitrogen source, then 8 aziridines, including aα-electron-withdrawing group aziridine and 7α-electron-donating group aziridines, was synthesized at the first step. NBS was used as the catalyst and shown excellent catalytic activity when catalyzing aziridination reaction ofα-electron- donating group alkenes, but when it comes toα-electron-withdrawing group olefins, the yield was poor: nearly no products obtained by the same method. After resorting to the relevant literature, Py·HBr3 was choosed as a catalyst to proceed the aziridination reaction ofα-electron-withdrawing group alkenes and Chloramine-T, then the corresponding product was obtained, and it was proved that Py·HBr3 has the activity in catalyzing the aziridination reaction of both theα-electron-withdrawing or donating group olefins. Meanwhile, 15 imines was synthesized to proceed the addition reaction of carbine and imines. CHCl3 was choosed as solvent, in the presence of KOH, carbine generated and reacted with C=N bond of imines, finally 8 different aziridines was got. In the second part, glucose compounds was synthesized and selected as the nucleophilic reagent in the ring-opening reaction of aziridines. We chose 4 different aziridines as the substrate, and then obtained the corresponding ring-opening products in good yield. In the third part, a new chiral ligand and two lactone perfumes was synthesized, and it pave the way of the asymmetric synthesis and regio-selective ring-opening of the aziridines.