Synthesis of optically active 1-aza-4-oxabicyclo[4.1.0]-heptan-5-ones |
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Authors: | 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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Institution: | (1) Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006 Riga;(2) Institute of Chemical Physics, Academy of Sciences of the USSR, 117977 Moscow |
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Abstract: | The reaction of the methyl ester of 1,2-dibromopropionic acid with chiral - aminoalcohols under the conditions of the Gabriel-Cromwell reaction gave epimers of methyl 1-( -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-( -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-oxabicyclo4,1,0]heptan-5-ones in solution is a distorted boat.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 975–980, July, 1989. |
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