Enantioresolution and absolute configurations of chiral meta-substituted diphenylmethanols as determined by X-ray crystallographic and 1H NMR anisotropy methods

被引:18
作者
Kosaka, M
Sugito, T
Kasai, Y
Kuwahara, S
Watanabe, M
Harada, N
Job, GE
Shvet, A
Pirkle, WH
机构
[1] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Aoba Ku, Sendai, Miyagi 9808577, Japan
[2] Univ Illinois, Sch Chem Sci, Urbana, IL 61801 USA
关键词
chiral phthalic acid; diastereomeric esters; HPLC separation on silica gel; internal standard of absolute configuration; chiral derivatizing agent; 2-metboxy-2-(1-naphthyl)propionic acid; M alpha NP acid;
D O I
10.1002/chir.10209
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
meta-Substituted diphenylmethanols were enantioresolved by the method of chiral phthalic acid yielding enantiopure alcohols. Their absolute configurations were unambiguously determined by X-ray crystallography of chiral phthalate esters and/or by the H-1 NMR anisotropy method using 2-methoxy-2-(1-naphthyl)propionic acid.
引用
收藏
页码:324 / 328
页数:5
相关论文
共 14 条
[1]  
Bolm C, 2000, ANGEW CHEM INT EDIT, V39, P3465, DOI 10.1002/1521-3773(20001002)39:19<3465::AID-ANIE3465>3.0.CO
[2]  
2-4
[3]  
Harada N, 2000, J PHYS ORG CHEM, V13, P422, DOI 10.1002/1099-1395(200007)13:7<422::AID-POC256>3.0.CO
[4]  
2-9
[5]   2-methoxy-2-(1-naphthyl)propionic acid, a powerful chiral auxiliary for enantioresolution of alcohols and determination of their absolute configurations by the 1H NMR anisotropy method [J].
Harada, N ;
Watanabe, M ;
Kuwahara, S ;
Sugio, A ;
Kasai, Y ;
Ichikawa, A .
TETRAHEDRON-ASYMMETRY, 2000, 11 (06) :1249-1253
[6]  
Harada N, 1998, ENANTIOMER, V3, P64
[7]  
Harada N, 1997, ENANTIOMER, V2, P359
[8]   REVISION OF THE ABSOLUTE-CONFIGURATIONS OF [8]PARACYCLOPHANE-10-CARBOXYLIC AND 15-METHYL[10]PARACYCLOPHANE-12-CARBOXYLIC ACIDS [J].
HARADA, N ;
SOUTOME, T ;
NEHIRA, T ;
UDA, H ;
OI, S ;
OKAMURA, A ;
MIYANO, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) :7547-7548
[9]  
Harada N, 1996, ENANTIOMER, V1, P35
[10]   Comparison of CD spectra of (2-methylphenyl)- and (2,6-dimethylphenyl)-phenylmethanols leads to erroneous absolute configurations [J].
Kosaka, M ;
Kuwahara, S ;
Watanabe, M ;
Harada, N ;
Job, GE ;
Pirkle, WH .
ENANTIOMER, 2002, 7 (4-5) :213-217