DIRECT SEPARATION OF CONE-SHAPED TRI-O-ALKYLATED CHIRAL CALIX[4]ARENES BY ENANTIOSELECTIVE HPLC

被引：14

作者：

CACCAMESE, S

PAPPALARDO, S

机构：

[1] Department of Chemical Sciences, University of Catania, Catania

来源：

CHIRALITY | 1993年 / 5卷 / 03期

关键词：

CHIRAL PHASES; INHERENTLY CHIRAL CALIXARENES; CD SPECTRA;

D O I：

10.1002/chir.530050310

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The direct HPLC separation of eight inherently chiral atropisomeric calix[4]arenes has been achieved using Chiralcel OD phase. A rationale is given for the variation of the enantioselectivity as a function of the 0-alkyl or 0-aryl groups. In closely related structures hydrogen bond formation between the free hydroxyl of the analyte and the chiral phase plays an important role in the chiral recognition process.

引用

收藏

页码：159 / 163

页数：5

相关论文

共 18 条

[1] ON THE CONFORMATIONAL ISOMERS IN TETRA-O-ALKYLCALIX[4]ARENES [J].

ARAKI, K ;

IWAMOTO, K ;

SHINKAI, S ;

MATSUDA, T .

CHEMISTRY LETTERS, 1989, (10) :1747-1750

[2] INDUCED CIRCULAR-DICHROISM IN CALIXARENE COMPLEXES [J].

ARIMURA, T ;

EDAMITSU, S ;

SHINKAI, S ;

MANABE, O ;

MURAMATSU, T ;

TASHIRO, M .

CHEMISTRY LETTERS, 1987, (11) :2269-2272

[3] A NEW ROUTE TO CHIRAL CALIX[4]ARENES VIA 1,3-DERIVATIZATION [J].

BOHMER, V ;

WOLFF, A ;

VOGT, W .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (14) :968-970

[4]

BOHMER V, 1987, J ORG CHEM, V52, P3200

[5] ASYMMETRICALLY-SUBSTITUTED CALIX(4)ARENES [J].

BOHMER, V ;

MERKEL, L ;

KUNZ, U .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (12) :896-897

[6] SYNTHESIS OF CALIX[4]ARENES PRESENTING NO PLANE OF SYMMETRY [J].

CASABIANCA, H ;

ROYER, J ;

SATRALLAH, A ;

TATYC, A ;

VICENS, J .

TETRAHEDRON LETTERS, 1987, 28 (52) :6595-6596

[7]

FERGUSON G, UNPUB

[8] CALIXARENES .22. SYNTHESIS, PROPERTIES, AND METAL COMPLEXATION OF AMINOCALIXARENES [J].

GUTSCHE, CD ;

NAM, KC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6153-6162

[9]

GUTSCHE CD, 1991, MONOGRAPHS SUPRAMOLE

[10] SYNTHESIS AND OPTICAL RESOLUTION OF A CHIRAL CALIX[4]ARENE ASYMMETRICALLY-SUBSTITUTED ON THE LOWER RIM [J].

IWAMOTO, K ;

YANAGI, A ;

ARIMURA, T ;

MATSUDA, T ;

SHINKAI, S .

CHEMISTRY LETTERS, 1990, (10) :1901-1904