PREPARATION OF CHIRAL BUILDING-BLOCKS AND AUXILIARIES BY CHROMATOGRAPHY ON CELLULOSE TRIACETATE (CTA I) - INDICATIONS FOR THE PRESENCE OF MULTIPLE INTERACTION SITES IN CTA I
PREPARATION OF CHIRAL BUILDING-BLOCKS AND AUXILIARIES BY CHROMATOGRAPHY ON CELLULOSE TRIACETATE (CTA I) - INDICATIONS FOR THE PRESENCE OF MULTIPLE INTERACTION SITES IN CTA I
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DOI：
10.1002/chir.530020104
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发表时间：
1990-01-01
期刊：
影响因子：
2
通讯作者：
WOLF, RM
中科院分区：
文献类型：
--
作者：
FRANCOTTE, E;WOLF, RM
由于对光学活性化合物的需求日益增加，提供光学纯同分异构体的方法的发展正在加紧进行。在这些方法中，手性固定相的色谱拆分是非常有前景的，尽管到目前为止只有少量的制备应用被报道。在这项工作中，我们证明了作为手性相的三醋酸酯纤维素I(CTA I)具有许多优点。CTA I的广泛适用性和高负载量是制备层析特别重要的特点。然而，对待拆分的外消旋体进行轻微的结构修改通常可以极大地提高拆分率。这一策略已经应用于许多实际问题，并以一些手性构筑块和助剂为例进行了说明。此外，系统地研究了苯环对位取代基对不同系列芳香族化合物的影响，得出结论：在CTA I的手性环境中，一定存在大量不同的相互作用部位。
Due to the increasing demand for optically active compounds, the development of methods supplying optically pure isomers is intensively progressing. Among these methods the chromatographic resolution on chiral stationary phases is very promising, although only a limited number of preparative applications have been reported so far. In this work, we demonstrate that especially cellulose triacetate I (CTA I) as a chiral phase presents a number of advantages for this purpose. The broad applicability and the high loading capacity of CTA I are particularly important features for preparative chromatography. Nevertheless, slight structural modifications of the racemates to be resolved can often strongly improve the resolution. This strategy has been appllied to numerous practical problems and is illustrated in this work taking as examples some chiral building blocks and auxiliaries. Moreover, a systematic investigation of the influence of a substituent in the para-position of the phenyl ring for different series of aromatic compounds led to the conclusion that a large number of different interaction sites must be present in the chiral environment of CTA I.