Conversion of 2-isoxazolines into aziridines by lithium aluminum hydride reduction

Abstract It is shown that the reduction of some of 2-isoxazolines with LAH gives the corresponding aziridines, in a wide range of yields depending upon the substituent effects of the 2-isoxazolines. For example, 2-isoxazolines bearing a Ph group at C 4 -position afford the aziridines in almost quantitative yields, but those having a Me group instead of the Ph group at the same position furnish the aziridines in poor yields. In addition, kinetics and mechanism of aziridine formation from 2-isoxazolines are examined in comparison with those of aziridine formation from an oxime and its O-methyl ether. This reaction is a simple and convenient method for the synthesis of aziridines.