Über die Enantiomerentrennung durch Verteilung zwischen flüssigen Phasen. 4. Mitteilung. Enantioselektivität der diastereoisomeren Weinsäure‐dimenthylester gegenüber α‐Aminoalkohol‐Salzen
作者:
Vladimir Prelog,
Miljenko Dumić,
期刊:
Helvetica Chimica Acta
(WILEY Available online 1986)
卷期:
Volume 69,
issue 1
页码: 5-11
ISSN:0018-019X
年代: 1986
DOI:10.1002/hlca.19860690103
出版商: WILEY‐VCH Verlag GmbH
数据来源: WILEY
摘要:
Separation of Enantiomers by Partition between Liquid Phases. Enantioselectivity of Diastereoisomeric Dimenthyl Tartarates towards α‐Aminoalcohol SaltsThe enantioselectivity of the easily obtainable diastereoisomeric dimenthyl tartaratesIandIItowards the salts of a series of α‐aminoalcohols1‐10was investigated by partition between aqueous and lipophilic phase. The measured enantiomer distribution constantsQ(=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)‐esterIis appreciably more selective than its (S,S)‐diastereoisomerIIor other previously investigated esters. The tartaratesI‐IIItransport norephedrin salts through bulk lipophilic membranes with enantioselectivity comparable to that observed in partition experiments. The most enantioselective esterIcan be used as an efficient mobile phase for preparative separation of norephedrine enantiomers by flash partition c
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