Conclusions
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1.
Total separation of the (−)-1S,5R,6S- and (+)-1R,5S,6R-enantiomers of the stable l,6-diazabicyclo[3.1.0]hexane-5-carboxylic acid is effected via the diastereoisomeric salts with l-ephedrine.
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2.
The diastereoisomeric α-phenylethylamides of l,6-diazabicyclo[3.1.0]hexane-5-carboxylic acid have been obtained in relatively low optical purity (10–12%) by amidating the methyl esters followed by recrystallization and the asymmetric epimination of Δ1-pyrroline-2-carboxylic acid S-α-phenylethylamide.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10 pp. 2266–2271, October, 1986.
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Shustov, G.V., Denisenko, S.N., Zolotoi, A.B. et al. Asymmetrical nitrogen. 51. Synthesis and optical activation of 1,6-diazabicyclo-[3.1.0]hexane-5-carboxylic acid and its derivatives. Russ Chem Bull 35, 2071–2076 (1986). https://doi.org/10.1007/BF00957527
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DOI: https://doi.org/10.1007/BF00957527