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Author(s): Kinbara K; Harada Y; Saigo K
Title: A high-performance, tailor-made resolving agent: remarkable enhancement of resolution ability by introducing a naphthyl group into the fundamental skeleton
Source: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 (7): 1339-1347
Date: 2000
Document Type: Journal : Article
DOI:
Language: English
Comment:
Address: Univ Tokyo, Dept Chem & Biotechnol, Grad Sch Engn, Bunkyo Ku, Tokyo 1138656, Japan.
Reprint: Saigo, K, Univ Tokyo, Dept Integrated Biosci, Grad Sch Frontier Sci,
Bunkyo Ku, Tokyo 1138656, Japan. E-mail:
Abstract: 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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