Enantiopure trans- and cis-3-aminoindan-1-ols:: Preparation and application as novel basic resolving agents

被引：18

作者：

Kinbara, K ^{[1
]}

Katsumata, Y ^{[1
]}

Saigo, K ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Frontier Sci, Dept Integrated Biosci, Bunkyo Ku, Tokyo 1138656, Japan

来源：

CHEMISTRY LETTERS | 2002年 / 03期

关键词：

D O I：

10.1246/cl.2002.266

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

trans- and cis-3-Aminoindan-1-ols were prepared by moderately selective reductions of 3-aminoindan-1-one derivatives and separated into enantiopure forms. The enantiopure transisomer had a moderate resolving ability for 2-arylalkanoic acids having a naphthalene ring at the a-position. The X-ray crystallographic analysis showed that an infinite hydrogen-bond sheet was formed in the less-soluble salt, suggesting that the skeleton of these indanols would be favorable for the stabilization of the less-soluble salt by hydrogen-bonding interaction.

引用

页码：266 / 267

页数：2

共 6 条

[1] Effect of a substituent on an aromatic group in diastereomeric resolution
Kinbara, K
Oishi, K
Harada, Y
Saigo, K
[J]. TETRAHEDRON, 2000, 56 (36) : 6651 - 6655
[2] Systematic study of chiral discrimination upon crystallisation. Part 2. Chiral discrimination of 2-arylalkanoic acids by (1R,2S)-2-amino-1,2-diphenylethanol
Kinbara, K
Kobayashi, Y
Saigo, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (08): : 1767 - 1775
[3] Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network
Kinbara, K
Kobayashi, Y
Saigo, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (01): : 111 - 119
[4] A high-performance, tailor-made resolving agent: remarkable enhancement of resolution ability by introducing a naphthyl group into the fundamental skeleton
Kinbara, K
Harada, Y
Saigo, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (07): : 1339 - 1347
[5] Chiral discrimination upon crystallisation of the diastereomeric salts of 1-arylethylamines with mandelic acid or p-methoxymandelic acid: Interpretation of the resolution efficiencies on the basis of the crystal structures
Kinbara, K
Sakai, K
Hashimoto, Y
Nohira, H
Saigo, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (12): : 2615 - 2622
[6] Asymmetric synthesis of the alkaloids mayfoline and N(1)-acetyl-N(1)-deoxymayfoline
Kuehne, P
Linden, A
Hesse, M
[J]. HELVETICA CHIMICA ACTA, 1996, 79 (04) : 1085 - 1094

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