The Enantiomeric Differentiation Ability of Chiral Crown Ethers Based on Carbohydrates

被引：32

作者：

Bako, Peter ^{[1
]}

Keglevich, Gyoergy ^{[1
]}

Rapi, Zsolt ^{[1
]}

ToKe, Laszlo ^{[2
]}

机构：

[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary

[2] Hungarian Acad Sci, Dept Organ Chem & Technol, Res Grp Organ Chem Technol, Budapest, Hungary

来源：

CURRENT ORGANIC CHEMISTRY | 2012年 / 16卷 / 03期

基金：

匈牙利科学研究基金会;

关键词：

Chiral crown ethers; carbohydrate-based crown ethers; enantiomeric recognition; enantiomer separation; HOST-GUEST COMPLEXATION; AMINO-ACID ENANTIOMERS; STATIONARY-PHASE; D-MANNITOL; D-GLUCOSE; AZACROWN ETHERS; ESTER SALTS; CHROMATOGRAPHIC RESOLUTION; MACROCYCLIC RECEPTORS; ENZYME ANALOGS;

D O I：

10.2174/138527212799499877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiomeric differentiation ability of chiral sugar-based crown ethers can be utilized for the determination of the enantiomeric composition of chiral amino compounds and for the separation of racemic amino compounds. Chiral crown ethers incorporating various carbohydrate units in the macrocyclic structure showing enantiomeric recognition towards chiral primary amines, amino acids and amino acid esters are reviewed here. The chiral recognition of organic ammonium salts by crown ethers may be tested with various methods. In this review, practical applications are also summarized, where the enantiomers of racemic amino compounds and their derivatives are separated by carbohydrate-based crown ethers immobilized on a stationary phase.

引用

页码：297 / 304

页数：8

共 61 条

[1]

[Anonymous], 1981, PROGR MACROCYCLIC CH

[2] Novel monoaza- and diazacrown ethers incorporating sugar units and their extraction ability towards picrate salts [J].

Bako, P ;

Toke, L .

JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1995, 23 (03) :195-201

[3] Synthesis of D-mannose-based azacrown ethers and their application in enantioselective reactions [J].

Bakó, P ;

Makó, A ;

Keglevich, G ;

Kubinyi, M ;

Pál, K .

TETRAHEDRON-ASYMMETRY, 2005, 16 (10) :1861-1871

[4] Chiral azacrown ethers derived from D-glucose as catalysts for enantioselective Michael addition [J].

Bako, P ;

Kiss, T ;

Toke, L .

TETRAHEDRON LETTERS, 1997, 38 (41) :7259-7262

[5] Synthesis and application in asymmetric synthesis of azacrown ethers derived from D-glucose [J].

Bakó, P ;

Vizvárdi, K ;

Bajor, Z ;

Toke, L .

CHEMICAL COMMUNICATIONS, 1998, (11) :1193-1194

[6] Asymmetric C-C bond forming reactions with chiral crown catalysts derived from D-glucose and D-galactose [J].

Bakó, P ;

Czinege, E ;

Bakó, T ;

Czugler, M ;

Toke, L .

TETRAHEDRON-ASYMMETRY, 1999, 10 (23) :4539-4551

[7] Asymmetric Phase Transfer Reactions Catalyzed by Chiral Crown Ethers Derived from Monosaccharides [J].

Bako, Peter ;

Keglevich, Gyoergy ;

Rapi, Zsolt .

LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (08) :645-656

[8]

BURKERT U, 1982, ACS MONOGRAPH, V177

[9] Complexation of some amine compounds by macrocyclic receptors [J].

Buschmann, HJ ;

Mutihac, L ;

Jansen, K .

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2001, 39 (1-2) :1-11

[10] DESIGN OF COMPLEXES BETWEEN SYNTHETIC HOSTS AND ORGANIC GUESTS [J].

CRAM, DJ ;

CRAM, JM .

ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (01) :8-14

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