Preparation of homochiral azophenolic crown ethers containing 1-phenyltethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: Enantiomer recognition behaviour towards chiral 2-aminoethanol derivatives

被引:18
作者
Naemura, K
Ogasahara, K
Hirose, K
Tobe, Y
机构
[1] Department of Chemistry, Faculty of Engineering Science, Osaka University, Toyonaka
关键词
D O I
10.1016/S0957-4166(96)00472-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiomerically pure azophenolic crown ethers 1-4 containing (S)- or (R)-1-phenylethane-1,2-diol moieties and (2S,4S)-2,4-dimethyl-3-oxapentane-1,5-diol moiety as a chiral subunit were prepared; crown ethers (S,S,S,S)-1 showed high chiral recognition behaviour in complexation with 2-substituted 2-aminoethanol derivatives. (C) 1997 Published by Elsevier Science Ltd.
引用
收藏
页码:19 / 22
页数:4
相关论文
共 8 条
[1]  
FEUTRILL GI, 1970, TETRAHEDRON LETT, V16, P1327
[2]   RECOGNITION BY NEW SYMMETRICALLY SUBSTITUTED CHIRAL DIPHENYL-BUTYLPYRIDINO-18-CROWN-6 AND DI-TERT-BUTYLPYRIDINO-18-CROWN-6 AND ASYMMETRICALLY SUBSTITUTED CHIRAL DIMETHYLPYRIDINO-18-CROWN-6 LIGANDS OF THE ENANTIOMERS OF VARIOUS ORGANIC AMMONIUM PERCHLORATES [J].
HUSZTHY, P ;
BRADSHAW, JS ;
ZHU, CY ;
IZATT, RM ;
LIFSON, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3330-3336
[3]  
Lehn J. M., 1995, SUPRAMOLECULAR CHEM
[4]   PREPARATION AND ENANTIOMER RECOGNITION OF CHIRAL AZOPHENOLIC CROWN-ETHERS HAVING 3 CHIRAL BARRIERS ON EACH OF THE HOMOTOPIC FACES [J].
NAEMURA, K ;
ASADA, M ;
HIROSE, K ;
TOBE, Y .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1873-1876
[5]   Preparation and enantiomer recognition behaviour of azophenolic crown ethers containing cis-1-phenylcyclohexane-1,2-diol as the chiral subunit and 2,4-dinitrophenylazophenol as the chromophore [J].
Naemura, K ;
Ueno, K ;
Takeuchi, S ;
Hirose, K ;
Tobe, Y ;
Kaneda, T ;
Sakata, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (04) :383-388
[6]   PREPARATION AND ENANTIOMER RECOGNITION BEHAVIOR OF AZOPHENOLIC CROWN-ETHERS CONTAINING CIS-CYCLOHEXANE-1,2-DIOL AS THE CHIRAL CENTER [J].
NAEMURA, K ;
TAKEUCHI, S ;
HIROSE, K ;
TOBE, Y ;
KANEDA, T ;
SAKATA, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (03) :213-219
[7]   AZOPHENOLIC ACERANDS HAVING CHIRAL 1-PHENYL-CIS-1,2-CYCLOHEXANEDIOL UNITS - A CORRELATION BETWEEN ENANTIORECOGNITIVE COLORATION AND HOST-GUEST COMPLEMENTARITY [J].
NAEMURA, K ;
UENO, K ;
TAKEUCHI, S ;
TOBE, Y ;
KANEDA, T ;
SAKATA, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8475-8476
[8]   MOLECULAR ADDITION COMPOUNDS OF IODINE .1. AN ABSOLUTE METHOD FOR THE SPECTROSCOPIC DETERMINATION OF EQUILIBRIUM CONSTANTS [J].
ROSE, NJ ;
DRAGO, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (23) :6138-6141