A brief review of Cn-symmetric calixarenes and resorcinarenes

被引:82
作者
McIldowie, M. J. [1 ]
Mocerino, M. [1 ]
Ogden, M. I. [1 ]
机构
[1] Curtin Univ Technol, Dept Appl Chem, Perth, WA, Australia
关键词
calixarene; resorcinarene; chirality; dissymmetry; INTRAMOLECULAR RING-CLOSURE; OPTICAL RESOLUTION; SELECTIVE DERIVATIZATION; ENANTIOMERICALLY PURE; DISSYMMETRIC CALIX<4>ARENES; DERIVATIVES; RESORCARENES; COMPLEXATION; CONE; INTERCONVERSION;
D O I
10.1080/10610270902980663
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Calixarene and resorcinarene macrocycles are renowned for their ability to form inclusion complexes or act as molecular scaffolds. The addition of chirality to these non-planar molecules is an exciting enhancement of their already robust potential, offering much promise as ligands for chiral catalysis and enantioselective separations. Chiral calixarenes can be produced by the attachment of a chiral moiety or by the placement of an achiral functionality on the macrocyclic structure so as to render it asymmetric. The latter method is particularly intriguing, often resulting in molecules which have C-n dissymmetry. This review describes examples of the C-n-dissymmetric calixarenes and resorcinarenes prepared to date and discusses aspects of their chirality, including their pictorial and written descriptors.
引用
收藏
页码:13 / 39
页数:27
相关论文
共 91 条
[1]   Extraannular fluorinated calixarenes:: Regiospecificity of the deoxofluorination reactions of bis(spirodienol) derivatives [J].
Agbaria, K ;
Wöhnert, J ;
Biali, SE .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :7059-7066
[2]  
Agena C, 2001, EUR J ORG CHEM, V2001, P2977, DOI 10.1002/1099-0690(200108)2001:15<2977::AID-EJOC2977>3.0.CO
[3]  
2-L
[4]   Selective derivatisation of resorcarenes .1. The regioselective formation of tetra-benzoxazine derivatives [J].
Airola, K ;
Bohmer, V ;
Paulus, EF ;
Rissanen, K ;
Schmidt, C ;
Thondorf, I ;
Vogt, W .
TETRAHEDRON, 1997, 53 (31) :10709-10724
[5]   CHLOROMETHYLATION OF CALIXARENES AND SYNTHESIS OF NEW WATER-SOLUBLE MACROCYCLIC HOSTS [J].
ALMI, M ;
ARDUINI, A ;
CASNATI, A ;
POCHINI, A ;
UNGARO, R .
TETRAHEDRON, 1989, 45 (07) :2177-2182
[6]   DISSYMMETRIC CALIX[4]ARENES WITH C4-SYMMETRY AND C2-SYMMETRY - SYNTHESIS, X-RAY STRUCTURES, CONFORMATIONAL FIXATION, AND H-1-NMR SPECTROSCOPIC STUDIES [J].
ANDREETTI, GD ;
BOHMER, V ;
JORDON, JG ;
TABATABAI, M ;
UGOZZOLI, F ;
VOGT, W ;
WOLFF, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :4023-4032
[7]   REGIOSELECTIVE AND DIASTEREOSELECTIVE CONDENSATION OF RESORCARENES WITH PRIMARY AMINES AND FORMALDEHYDE [J].
ARNECKE, R ;
BOHMER, V ;
FRIEBE, S ;
GEBAUER, S ;
KRAUSS, GJ ;
THONDORF, I ;
VOGT, W .
TETRAHEDRON LETTERS, 1995, 36 (35) :6221-6224
[8]   SYNTHESIS OF [1.1.1.1] (1,3)-2-METHOXYAZULENOPHANE - AZULENE ANALOG OF CALIXARENES [J].
ASAO, T ;
ITO, S ;
MORITA, N .
TETRAHEDRON LETTERS, 1988, 29 (23) :2839-2842
[9]   Studies on calix(aza)crowns, II.: Synthesis of novel proximal doubly bridged calix[4]arenes by intramolecular ring closure of syn 1,3- and 1,2-ω-chloroalkylamides [J].
Bitter, I ;
Grün, A ;
Tóth, G ;
Balázs, B ;
Horváth, G ;
Toke, L .
TETRAHEDRON, 1998, 54 (15) :3857-3870
[10]   INHERENTLY CHIRAL CALIXARENES [J].
BOHMER, V ;
KRAFT, D ;
TABATABAI, M .
JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1994, 19 (1-4) :17-39