124931-64-2Relevant academic research and scientific papers
SYNTHESIS OF OPTICALLY ACTIVE 1-AZA-4-OXABICYCLOHEPTAN-5-ONES
Krutius, O. N.,Eremeev, A. V.,Polyak, F. D.,Shustov, G. V.,Voznesenskii, V. N.,et al.
, p. 818 - 823 (1989)
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-oxabicycloheptan-5-ones is a function of the intramolecular contacts of the reacting OH and CO2Me groups in the lactonization of the cis-isomer.The most favorable conformation of the six-membered ring in 1-aza-4-oxabicycloeptan-5-ones in solution is a distorted boat.
Asymmetric nitrogen-lxxi. Asymmetric synthesis and lactonization of 1-β-hydroxyalkylaziridine-2-carboxylic esters into 4-oxa-1-azabicyclo[4.1.0]heptan-5-ones
Shustov,Krutius,Voznesensky,Chervin,Eremeev,Kostyanovsky,Polyak
, p. 6741 - 6752 (2007/10/02)
Epimeric mixtures of 1-β-hydroxyalkyl ziridlne-il-carboxylic esters were prepared by the Gabriel-Cromwell reaction, followed by their separation by liquid chromatography with subsequent lactonization of each epimer in the presence of base to give pure ena
