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Synthesis of optically active 1-aza-4-oxabicyclo[4.1.0]-heptan-5-ones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of the methyl ester of 1,2-dibromopropionic acid with chiral Β- aminoalcohols under the conditions of the Gabriel-Cromwell reaction gave epimers of methyl 1-(Β-hydroxyalkyl)aziridine-2-carboxylates, which were separated by liquid chromatography. NMR spectroscopy and CD were used to determine the absolute configuration of these products. The relative rate of conversion of epimeric esters of trans-1-(Β-hydroxyalkyl)aziridine-2-carboxylic acids to 1-aza-4- oxabicyclo-[4.1.0]heptan-5-ones is a function of the intramolecular contacts of the reacting OH and CO2Me groups in the lactonization of the cis isomers. The most favorable conformation of the six-membered ring in 1-aza-4-oxabicyclo[4,1,0]heptan-5-ones in solution is a distorted boat.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006, Riga

    O. N. Krutius, A. V. Eremeev, F. D. Polyak, G. V. Shustov, V. N. Voznesenskii, I. I. Chervin & R. G. Kostyanovskii

  2. Institute of Chemical Physics, Academy of Sciences of the USSR, 117977, Moscow

    O. N. Krutius, A. V. Eremeev, F. D. Polyak, G. V. Shustov, V. N. Voznesenskii, I. I. Chervin & R. G. Kostyanovskii

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  1. O. N. Krutius
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  2. A. V. Eremeev
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  3. F. D. Polyak
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  4. G. V. Shustov
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  5. V. N. Voznesenskii
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  6. I. I. Chervin
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  7. R. G. Kostyanovskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 975–980, July, 1989.

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Krutius, O.N., Eremeev, A.V., Polyak, F.D. et al. Synthesis of optically active 1-aza-4-oxabicyclo[4.1.0]-heptan-5-ones. Chem Heterocycl Compd 25, 818–823 (1989). https://doi.org/10.1007/BF00472757

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  • DOI: https://doi.org/10.1007/BF00472757

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