Calix[4]arene, calix[4]resorcarene, and cyclodextrin derivatives and their lanthanide complexes as chiral NMR shift reagents

被引：33

作者：

Smith, KJ ^{[1
]}

Wilcox, JD ^{[1
]}

Mirick, GE ^{[1
]}

Wacker, LS ^{[1
]}

Ryan, NS ^{[1
]}

Vensel, DA ^{[1
]}

Readling, R ^{[1
]}

Domush, HL ^{[1
]}

Amonoo, EP ^{[1
]}

Shariff, SS ^{[1
]}

Wenzel, TJ ^{[1
]}

机构：

[1] Bates Coll, Dept Chem, Lewiston, ME 04240 USA

来源：

CHIRALITY | 2003年 / 15卷

关键词：

NMR; chiral shift reagents; calixarenes; calixresorcarenes; cyclodextrins; enantiomeric excess; lanthanide shift reagents; chiral solvating agents;

D O I：

10.1002/chir.10254

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Calix[4]arenes, calix[4]resorcarenes, and anionic cyclodextrin derivatives were examined as chiral NMR solvating agents. The calix[4]arenes were prepared by attachment of amino acids through the hydroxyl groups of the phenol rings. Chloroform-, methanol-, and water-soluble derivatives were prepared and tested with a range of substrates. Chloroform-soluble chiral calix[4]resorcarenes were prepared by attachment of chiral primary and secondary amines and examined in NMR applications with a variety of substrates. Sulfated and carboxymethylated beta-cyclodextrin are effective at causing enantiomeric discrimination in the H-1 NMR spectra of organic cations. Lanthanide ions associate at the carboxymethyl groups and cause sizeable shifts and enhancements in enantiomeric discrimination in the spectra of organic cations. The enhancements caused by the lanthanide ion are large enough that much lower concentrations of the cyclodextrin can be used as compared to conventional analyses. (C) 2003 Wiley-Liss, Inc.

引用

页码：S150 / S158

页数：9

共 38 条

[1] REGIOSELECTIVE AND DIASTEREOSELECTIVE CONDENSATION OF RESORCARENES WITH PRIMARY AMINES AND FORMALDEHYDE [J].