Über die Enantiomerentrennung durch Verteilung zwischen flüssigen Phasen. 3. Mitteilung. Selektivität der lipophilen Weinsäureester für chirale Ammonium-Salze verschiedener Konstitution und Konfiguration

Separation of Enantiomers by Partition between Liquid Phases. 3. Communication. Selectivity of Lipophilic Tartaric Acid Esters for Chiral Ammonium Salts of Different Constitution and Configuration Several methods are described which allow determination on a small scale of the enantiomer distribution constant Q, and the affinity coefficient P, which characterize the enantioselectivity and the affinity of a lipophilic phase for ammonium salts of different constitution and configuration. The influence of concentration of the tartaric acid ester, temperature, concentration and type of the lipophilic anion on Q and P was investigated to find out favourable experimental conditions for resolutions of racemates by iterative process, e.g. partition chromatography. The relationship between Q and the configuration of aminoalcohols 1–12 was explored and the observed regularities are pointed out. In addition it was found that lipophilic tartaric acid esters are enantioselective to salts of threo-1,2-diphenyl-1,2-ethanediamine 13 , and to phenylglycine and its derivatives 14–16.