Abstract
It was found using the1H and13C NMR methods that (2R, 12R)-disubstituted derivatives of 18-crown-6-ether containing the residues of l,3∶2,4-di-O-ethylidene(Ia) and 1,3∶2,4-di-O-benzylidene-D-sorbitol (IIa) as substituents and 1,4∶3,6dianhydro-D-mannito-18-crown-6 (III) form stable 1∶1 complexes with α-phenylethylammonium, O-methyl-α-phenylglycinium, O-methylalaninium, O-methyl-α-phenylalaninium, O-methylglycinium hexafluorophosphates, and display an enantiodifferentiating ability with respect to racemates of these salts. In the extraction of the chiral ammonium salts, coronand (Ia) exhibits a low (DCE 1.091.10) enantioselectivity with respect to (R)-enantiomers of α-phenylethyl ammonium and O-methyl-α-phenylglycinium hexafluorophosphates, while coronand (IIa) displays enantioselectivity with respect to (S)-enantiomer of the latter (DCE 0.82). Coronand (III) does not display enantioselectivity in complexes with racemates of these salts.
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For previous communication, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2492–2500, November, 1989.
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Struchkova, M.I., Él'perina, E.A., Abylgaziev, R.I. et al. Chiral complex-forming and trans-phase transfer agents. 6.1E and13C NMR study of complex-forming ability of homotopic 18-crown-6-ethers based on D-sorbitol and D-mannitol with chiral ammonium salts. Russ Chem Bull 38, 2286–2294 (1989). https://doi.org/10.1007/BF01168071
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DOI: https://doi.org/10.1007/BF01168071