Chiral discrimination of 2-arylalkanoic acids by (1S,2S)-1-aminoindan-2-ol and (1S,2S)-2-aminoindan-1-ol:: Correlation of the relative configuration of the amino and hydroxy groups with the pattern of a supramolecular hydrogen-bond network in the less-soluble diastereomeric salt

被引：11

作者：

Kinbara, K ^{[1
]}

Katsumata, Y ^{[1
]}

Saigo, K ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Frontier Sci, Dept Integrated Biosci, Chiba 2778562, Japan

来源：

CHIRALITY | 2003年 / 15卷 / 06期

关键词：

optical resolution; diastereomeric salt; crystal engineering; amino alcohol; 2-arylalkanoic acid;

D O I：

10.1002/chir.10202

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The diastereomeric resolution of 2-arylalkanoic acids with enantiopure trans-1-aminoindan-2-ol and trans-2-aminoindan-1-ol were studied. Enantiopure trans-1-aminoindan-2-ol had a moderate resolving ability for 2-arylalkanoic acids having a naphthyl group as an aryl substituent at the alpha-position, while enantiopure trans-2-aminoindan-1-ol had a moderate-to-high resolving ability for a wide variety of the acids having a methyl group as an alkyl substituent at the alpha-position. The crystal structures of the corresponding less-soluble salts revealed that a reinforced columnar hydrogen-bond network was formed in the less-soluble salts with trans-1-aminoindan-2-ol, while a rather stable hydrogen-bond sheet was generated with the assistance of water molecules in the less-soluble salts with trans-2-aminoindan-1-ol. These results suggest that not only the relative configuration but also the position of the hydrogen-bonding groups in resolving agents have a considerable effect on the structure of the less-soluble salts. The difference in favorable hydrogen-bond structure determined the adaptivity to the structural feature of target racemic 2-arylalkanoic acids in the resolution by trans-1-aminoindan-2-ol and trans-1-aminoindan-2-ol, respectively.

引用

页码：564 / 570

页数：7

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