Reaction of 1-alkyl-2-aryl-3-(2-methyl-2,3-epoxypropionyl)aziridines with boron trifluoride etherate in methanol

The reaction of boron trifluoride etherate in methanol with trans-1-methyl(ethyl)-or cis-1-cyclohexyl-2-aryl-3-(2-methyl-2,3-epoxypropionyl)aziridines leads to the formation of the corresponding boron fluoride complexes on the nitrogen atom of the aziridine ring. Reaction with trans-1-cyclohexyl-2-phenyl-3-(2-methyl-2,3-epoxypropionyl)aziridines occurs with stereospecific opening of the aziridine ring to give diastereomeric 2-methyl-5-methoxy-5-phenyl-4-cyclohexylamino-1,2-epoxypen-tan-3-ones, as well as products from the opening of the epoxide and aziridine rings — tetrahydrofuranones and tetrahydropyranones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 596–600, May, 1986.