Abstract
The reaction of 2,3-dibromopropanoates with 2-amino-2-methyl-1-propanol in the presence of triethylamine gave a number of 1-(2-hydroxy-1,1-dimethylethyl)aziridine-2-carboxylic acid esters, which, under the influence of basic catalysts, were converted to a bicyclic lactone — 2,2-dimethyl-4-oxa-1-azabicyclo[4.1.0]heptan-5-one. The effect of the structure of the substrate and the nature of the lactonizing agent on the rate of cyclization was studied. Two new catalysts for the cyclization of hydroxy esters to lactones, viz., CsF/Al2O3 and Cs2CO3/18-crown-6, are proposed.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1340–1343, October, 1988.
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Krutius, O.N., Polyak, F.D. & Eremeev, A.V. Synthesis and lactonization of 1-(2-hydroxy-1,1-dimethylethyl)-aziridine-2-carboxylic acid esters. Chem Heterocycl Compd 24, 1109–1112 (1988). https://doi.org/10.1007/BF00475684
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DOI: https://doi.org/10.1007/BF00475684