2-Naphthol as a powerful chromophore for the configurational assignment of carboxylic acid groups via the CD exciton chirality method

被引:15
作者
Hartl, M [1 ]
Humpf, HU [1 ]
机构
[1] Univ Wurzburg, Lehrstuhl Lebensmittelchem, D-97074 Wurzburg, Germany
关键词
D O I
10.1016/S0957-4166(00)00116-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel approach for the stereochemical assignment of carboxylic acid groups via the circular dichroism (CD) exciton chirality method using the 2-naphthyl chromophore is described. Direct esterification of carboxyl groups with 2-naphthol was effectively achieved with the employment of N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride as the activating reagent. The method was tested with several model compounds, including both cyclic and acyclic dicarboxylic acids, and also applied to the natural product abietic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1741 / 1747
页数:7
相关论文
共 13 条
[1]  
AkritopoulouZanze I, 1997, CHIRALITY, V9, P699, DOI 10.1002/(SICI)1520-636X(1997)9:7<699::AID-CHIR11>3.0.CO
[2]  
2-I
[3]  
DIAGOMESEGUER J, 1980, SYNTHESIS-STUTTGART, P547
[4]   A new exciton-coupled circular dichroism method for assigning the absolute configuration in acyclic alpha- and beta-hydroxy carboxylic acids [J].
Gimple, O ;
Schreier, P ;
Humpf, HU .
TETRAHEDRON-ASYMMETRY, 1997, 8 (01) :11-14
[5]  
Harada N, 1996, ENANTIOMER, V1, P119
[6]  
HARADA N, 1983, CICULAR DICHROIC SPE
[7]   Assigning the absolute configuration of fumonisins by the circular dichroism exciton chirality method [J].
Hartl, M ;
Humpf, HU .
TETRAHEDRON-ASYMMETRY, 1998, 9 (09) :1549-1556
[8]   Absolute configurational assignment of acyclic hydroxy carboxylic acids:: A new strategy in exciton-coupled circular dichroism [J].
Hör, K ;
Gimple, O ;
Schreier, P ;
Humpf, HU .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02) :322-325
[9]  
HOR K, 1998, NATURAL PRODUCT ANAL, P223
[10]  
NAKANISHI K, 1994, CIRCULAR DICHROISM P, P361