Synthesis of new chiral calix[4]arene diamide derivatives for liquid phase extraction of α-amino acid methylesters

被引:58
作者
Kocabas, Erdal [1 ]
Karakucuk, Aysegul [1 ]
Sirit, Abdulkadir [1 ]
Yilmaz, Mustafa [1 ]
机构
[1] Selcuk Univ, Dept Chem, TR-42031 Konya, Turkey
关键词
D O I
10.1016/j.tetasy.2006.05.016
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of chiral diamide derivatives of calix[4]arene from the reaction of p-tert-butylcalix[4]arene diester la and calix[4]arene diester 1b with various amino alcohols were reported. The H-1 and C-13 NMR, data showed that the compounds synthesized exist in the cone conformation. The extraction study properties of these new compounds 3a,b-4a,b towards some selected alpha-amino acid methylesters are also reported. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1514 / 1520
页数:7
相关论文
共 71 条
[1]   Chiral recognition of alpha-amino acid derivatives with a homooxacalix[3]arene: Construction of a pseudo-C-2-symmetrical compound from a C-3-symmetrical macrocycle [J].
Araki, K ;
Inada, K ;
Shinkai, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :72-74
[2]   Complexation of native L-α-aminoacids by water soluble calix[4]arenes [J].
Arena, G ;
Contino, A ;
Gulino, FG ;
Magrì, A ;
Sansone, F ;
Sciotto, D ;
Ungaro, R .
TETRAHEDRON LETTERS, 1999, 40 (08) :1597-1600
[3]   NEW WATER-SOLUBLE HOST CALIXARENES BEARING CHIRAL SUBSTITUENTS [J].
ARIMURA, T ;
KAWABATA, H ;
MATSUDA, T ;
MURAMATSU, T ;
SATOH, H ;
FUJIO, K ;
MANABE, O ;
SHINKAI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :301-306
[4]   Synthesis, optical resolution and complexation properties of inherently chiral monoalkylated p-tert-butyl-(1,2)-calix[4]crown ethers [J].
ArnaudNeu, F ;
Caccamese, S ;
Fuangswasdi, S ;
Pappalardo, S ;
Parisi, MF ;
Petringa, A ;
Principato, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8041-8048
[5]  
BAUM ST, 1980, CHEM LIFE SCI APPROA, P519
[6]   Synthesis of chiral 1,3-calix[4](crown-6) ethers as potential mediators for asymmetric recognition processes [J].
Bitter, I ;
Köszegi, É ;
Grün, A ;
Bakó, P ;
Pál, K ;
Grofcsik, A ;
Kubinyi, M ;
Balázs, B ;
Tóth, G .
TETRAHEDRON-ASYMMETRY, 2003, 14 (08) :1025-1035
[7]  
BLASCHKE G, 1979, ARZNEIMITTEL-FORSCH, V29-2, P1640
[8]   Synthesis of two calix[4]arene diamide derivatives for extraction of chromium(VI) [J].
Bozkurt, S ;
Karakucuk, A ;
Sirit, A ;
Yilmaz, M .
TETRAHEDRON, 2005, 61 (44) :10443-10448
[9]   Enzymatic synthesis of nonracemic inherently chiral calix[4]arenes by lipase-catalysed transesterification [J].
Browne, JK ;
McKervey, MA ;
Pitarch, M ;
Russell, JA ;
Millership, JS .
TETRAHEDRON LETTERS, 1998, 39 (13) :1787-1790
[10]   Synthesis of novel calixsugars:: Calix[4]arene-monosaccharide conjugates based on amide bonds [J].
Budka, J ;
Tkadlecová, M ;
Lhoták, P ;
Stibor, I .
TETRAHEDRON, 2000, 56 (13) :1883-1887