Über die Enantiomerentrennung durch Verteilung zwischen flüssigen Phasen. 4. Mitteilung. Enantioselektivität der diastereoisomeren Weinsäure‐dimenthylester gegenüber α‐Aminoalkohol‐Salzen
- 5 February 1986
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 69 (1) , 5-11
- https://doi.org/10.1002/hlca.19860690103
Abstract
Separation of Enantiomers by Partition between Liquid Phases. Enantioselectivity of Diastereoisomeric Dimenthyl Tartarates towards α‐Aminoalcohol SaltsThe enantioselectivity of the easily obtainable diastereoisomeric dimenthyl tartarates I and II towards the salts of a series of α‐aminoalcohols 1‐10 was investigated by partition between aqueous and lipophilic phase. The measured enantiomer distribution constants Q (=KA/KB) confirm the previously observed configurational relationships between the lipophilic tartarates and the preferentially extracted enantiomer of the hydrophilic ammonium slat. However, the (R,R)‐ester I is appreciably more selective than its (S,S)‐diastereoisomer II or other previously investigated esters. The tartarates I‐III transport norephedrin salts through bulk lipophilic membranes with enantioselectivity comparable to that observed in partition experiments. The most enantioselective ester I can be used as an efficient mobile phase for preparative separation of norephedrine enantiomers by flash partition chromatography.Keywords
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