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Über die Enantiomerentrennung durch Verteilung zwischen flüssigen Phasen. 4. Mitteilung . Enantioselektivität der diastereoisomeren Weinsäure‐dimenthylester gegenüber α‐Aminoalkohol‐Salzen
Author(s) -
Prelog Vladimir,
Dumić Miljenko
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690103
Subject(s) - chemistry , enantiomer , diastereomer , partition coefficient , aqueous solution , chromatography , stereochemistry , organic chemistry
Separation of Enantiomers by Partition between Liquid Phases. Enantioselectivity of Diastereoisomeric Dimenthyl Tartarates towards α‐Aminoalcohol Salts The 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 (= K A / K B ) 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.