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


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Article Info

DATE

1989-07

AUTHORS

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

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. More... »

PAGES

818-823

References to SciGraph publications

  • 1970. Nitrogen inversion in DYNAMIC STEREOCHEMISTRY
  • Identifiers

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    http://scigraph.springernature.com/pub.10.1007/bf00472757

    DOI

    http://dx.doi.org/10.1007/bf00472757

    DIMENSIONS

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