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
收藏
页码：564 / 570
页数：7
相关论文
共 50 条
  • [21] INTERORBITAL (1S, 2S) PAIR CORRELATION ENERGIES AND ABSOLUTE OVERLAP INTEGRALS
    LIGHT, SL
    PETERSSON, GA
    BULLETIN OF THE AMERICAN PHYSICAL SOCIETY, 1976, 21 (04): : 627 - 627
  • [22] Molecular structure studies of (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol
    Zhang, Tao
    Paluch, Krzysztof
    Scalabrino, Gaia
    Frankish, Neil
    Healy, Anne-Marie
    Sheridan, Helen
    JOURNAL OF MOLECULAR STRUCTURE, 2015, 1083 : 286 - 299
  • [23] 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
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (08): : 1767 - 1775
  • [24] β-amino alcohols derived from (1R,2S)-norephedrine and (1S,2S)-pseudonorephedrine as catalysts in the asymmetric addition of diethylzinc to aldehydes
    Parrott, Raleigh W., II
    Hitchcock, Shawn R.
    TETRAHEDRON-ASYMMETRY, 2008, 19 (01) : 19 - 26
  • [25] RELATIVE POPULATION OF THE LEVELS OF THE 1S 2S 2P AND 1S 2P2 CONFIGURATIONS OF ARGON FROM 3 ELECTRON EXCITED-STATES
    TUNNELL, TW
    BHALLA, CP
    BULLETIN OF THE AMERICAN PHYSICAL SOCIETY, 1980, 25 (07): : 780 - 780
  • [26] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF 2 DIASTEREOISOMERIC (1R,2S,3R) AND (1S,2S,3R)-2-AMINO-1-(2-FURYL)-1,3-BUTANDIOLS
    SZECHNER, B
    TETRAHEDRON, 1981, 37 (05) : 949 - 952
  • [27] A practical synthesis of Cbz protected (1R,2R) and (1S,2S) 2-hydroxy-cyclobutylamines
    Jin, Can
    Wang, Yilin
    Xu, Xiangsheng
    Li, Xiaoqing
    TETRAHEDRON LETTERS, 2025, 154
  • [28] Enantioselective synthesis of 2-substituted alcohols using (+)-(1S,2S)-pseudoephedrine as chiral auxiliary
    Tietze, Lutz F.
    Raith, Christian
    Brazel, C. Christian
    Hoelsken, Soeren
    Magull, Joerg
    SYNTHESIS-STUTTGART, 2008, 2 (02): : 229 - 236
  • [29] TOTAL ASYMMETRIC SYNTHESES OF (1S,2S)-NORCORONAMIC ACID, AND OF (1R,2R)- AND (1S,2S)-CORONAMIC ACIDS FROM THE DIASTEREOSELECTIVE CYCLIZATION OF 2-(N-BENZYLIDENEAMINO)-4-CHLOROBUTYRONITRILES
    GAUCHER, A
    OLLIVIER, J
    MARGUERITE, J
    PAUGAM, R
    SALAUN, J
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05): : 1312 - 1327
  • [30] Total asymmetric syntheses of (1S,2S)-norcoronamic acid, and of (1R,2R)- and (1S,2S)-coronamic acids from the diastereoselective cyclization of 2-(N-benzylideneamino)-4-chlorobutyronitriles
    Gaucher, Anne
    Ollivier, Jean
    Marguerite, Jacqueline
    Paugam, Renee
    Salaun, Jacques
    Canadian Journal of Chemistry, 1994, 72 (05)
12345