Liquid chromatographic separation of the enantiomers of antihistaminic 3,3′-di(1,3-thiazolidin-4-one) derivatives with two and four stereogenic centres
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- 作者：Caccamese ; Salvatore ; Principato ; Grazia ; Ottanà ; Rosaria ; Previtera ; Tindara ; Zappalà ; Carmela
- 刊名：Journal of Chromatography A
- 出版年：1995
- 出版时间：March 10, 1995
- 年：1995
- 卷：694
- 期：2
- 页码：355-363
- 全文大小：455 K
文摘
The enantiomers of anti-inflammatory and antihistaminic 3,3′-(1,2-ethanediyl)bis(2-aryl-1,3-thiazolidin-4-one) derivatives possessing two stereogenic centres were separated on Chiralcel OD stationary phase without derivatization. The meso form was also well separated from the enantiomers. The good resolution afforded a milligram-scale separation and subsequent measurement of the circular dichroism spectra of an enantiomeric pair. Addition of racemic α-mercaptopropionic acid to the N,N′-dibenzylideneethylenediamine yielded ten possible stereoisomers with four stereogenic centres. Two centres (2 and 2′) bear the same groups; the other two (5 and 5′) also bear the same groups, but these are different from the groups at 2 and 2′. In this situation four enantiomeric pairs and two meso forms exist; all of them were separated and identified using a Chiralpak AD column.