Synthesis and stereochemistry of 1-alkyl-2-aryl-3-(2-methyl-2,3-epoxypropionyl) aziridines

Two diastereoisomeric 1-alkyl-2-aryl-3-(2-methyl-2,3-epoxypropionyl) aziridines with an E configuration of the aziridine ring were obtained by the reaction of 2-methyl-2-cinnamoyoxiranes with iodine-methylamine and iodine-ethylamine complexes. The relative configuration of the chiral centers of the synthesized compounds was established by means of spectral data. The predominant formation of diastereomers with the RRR (SSS) relative configuration is explained by the effect of steric factors in the diastereomeric chelated amino enols that precede the formation of the epoxy keto aziridines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 880–883, July, 1980.