A high-performance, tailor-made resolving agent: remarkable enhancement of resolution ability by introducing a naphthyl group into the fundamental skeleton

被引:61
作者
Kinbara, K [1 ]
Harada, Y [1 ]
Saigo, K [1 ]
机构
[1] Univ Tokyo, Dept Chem & Biotechnol, Grad Sch Engn, Bunkyo Ku, Tokyo 1138656, Japan
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2000年 / 07期
关键词
D O I
10.1039/b000903m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel resolving agent, 2-naphthylglycolic acid (2-NGA), was designed for p-substituted 1-arylethylamines on the basis of the consideration that a rigid and large naphthyl group would be favorable for the close packing of supramolecular hydrogen-bond sheets formed between the carboxy groups of 2-NGA and the amino groups of p-substituted 1-arylethylamines. Racemic 2-NGA was readily available from commercially available raw materials, and both enantiopure forms could be obtained by simple diastereomeric resolution with enantiopure 1-phenylethylamine. Thus-prepared enantiopure 2-NGA was found to have an excellent resolution ability not only for p-substituted 1-arylethylamines, but also for a wide variety of chiral primary amines. X-Ray crystallographic analyses of the less- and more-soluble diastereomeric salts revealed that this excellent resolution ability of 2-NGA arose from the formation of a supramolecular hydrogen-bond sheet with the primary amine, as we had expected, and also from the possible achievement of an infinite chain of CH ...pi interaction between its naphthyl group and the aromatic group of the amine, which was formed in the hydrophobic region of the supramolecular hydrogen-bond sheet.
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页码:1339 / 1347
页数:9
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