New data on derivatives of 1-alkoxyaziridine-2-carboxylic acids

Esters of β-alkoxyamino-α-bromopropionic acids were obtained by reaction of α,β-dibromopropionic acid esters with alkoxyamines in the presence of triethylamine at 20°C for 1 month. When the products are refluxed in acetonitrile in the presence of triethylamine, they are converted to aziridines. Selective amidation of the alkoxyaziridines with excess dimethylamine in absolute methanol in the presence of sodium methoxide leads to enrichment with the cis isomer. The parameters of inversion of the nitrogen atom in the alkoxyaziridines were determined. Communication 20 from the series “Asymetric Unbridged Nitrogen”; see [1] for communication 19. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 212–215. February, 1980.