Chirality induction on achiral N-methyl aromatic amide oligomers bearing terminal carboxy groups with chiral Amines

被引:20
作者
Nishimura, T [1 ]
Maeda, K [1 ]
Yashima, E [1 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Dept Mol Design & Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan
关键词
N-methyl aromatic amide; induced circular dichroism; acid-base; optically active; absolute configuration; chiral discrimination;
D O I
10.1002/chir.20028
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Novel unsymmetrical N-methyl aromatic amide oligomers bearing two carboxy groups at both ends were synthesized and their complexation with various optically active amines in solution was investigated using circular dichroism (CD) spectroscopy. The complexes showed a characteristic induced CD in the absorption region due to the aromatic amide reflecting the absolute configuration of the chiral amines. (C) 2004 Wiley-Liss, Inc.
引用
收藏
页码:S12 / S22
页数:11
相关论文
共 39 条
[1]   Induced circular dichroism by chiral molecular interaction [J].
Allenmark, S .
CHIRALITY, 2003, 15 (05) :409-422
[2]   TOTAL ASYMMETRIC TRANSFORMATION OF AN N-METHYLBENZAMIDE [J].
AZUMAYA, I ;
YAMAGUCHI, K ;
OKAMOTO, I ;
KAGECHIKA, H ;
SHUDO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9083-9084
[3]   STEREOCHEMISTRIES OF AROMATIC N-METHYLAMIDES IN CRYSTAL AND SOLUTION - TEMPERATURE-DEPENDENT CONFORMATIONAL CONVERSION AND ATTRACTING AROMATIC-AROMATIC INTERACTIONS [J].
AZUMAYA, I ;
KAGECHIKA, H ;
YAMAGUCHI, K ;
SHUDO, K .
TETRAHEDRON, 1995, 51 (18) :5277-5290
[4]   Facile formation of aromatic cyclic N-methylamides based on cis conformational preference [J].
Azumaya, I ;
Kagechika, H ;
Yamaguchi, K ;
Shudo, K .
TETRAHEDRON LETTERS, 1996, 37 (28) :5003-5006
[5]  
Canary JW, 2001, ENANTIOMER, V6, P181
[6]   PI-STACKING AND THE PLATINUM-CATALYZED ASYMMETRIC HYDROFORMYLATION REACTION - A MOLECULAR MODELING STUDY [J].
CASTONGUAY, LA ;
RAPPE, AK ;
CASEWIT, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7177-7183
[7]   Metal hydride mediated reduction of 3-(alkylthio)oxindoles containing other potentially reducible groups [J].
Connolly, TJ ;
Durst, T .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (05) :536-541
[8]  
Connors K. A, 1987, BINDING CONSTANTS ME
[9]   A macrobicyclic receptor with versatile recognition properties: Simultaneous binding of an ion pair and selective complexation of dimethylsulfoxide [J].
Deetz, MJ ;
Shang, M ;
Smith, BD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) :6201-6207
[10]   Macromolecular chirality induction on optically inactive poly(4-carboxyphenyl isocyanide) with chiral amines: A dynamic conformational transition of poly(phenyl isocyanide) derivatives [J].
Ishikawa, M ;
Maeda, K ;
Yashima, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7448-7458