Stereochemistry of aziridine formation from ketoximes of bridged ring systems by lithium aluminum hydride reduction on benzobicylo[3.2.1]octenone oximes☆

Abstract In order to study further the applicability and stereochemistry of aziridine formation by LAH reduction of ketoximes of bridged ring systems, several ketones having the benzobicyclo[3.2.1]octene ring system have been synthesized by suitable methods. Separation of syn - and anti -isomers of the corresponding ketoximes and GLC analyses of reduction products have been performed. Although the effects of the benzene ring fused to the bridged rings on aziridine formation involving endo and exo ratio of the formed aziridines remain uncertain, the results clearly indicate that aziridine formation strongly depends upon the configurations of the oximes and occurs preponderantly from the syn -oximes.