A macrocyclic receptor for the chiral recognition of hydroxycarboxylates

被引：81

作者：

Tejeda, A ^{[1
]}

Oliva, AI ^{[1
]}

Simón, L ^{[1
]}

Grande, M ^{[1
]}

Caballero, MC ^{[1
]}

Morán, JR ^{[1
]}

机构：

[1] Univ Salamanca, Dept Quim Organ, E-37008 Salamanca, Spain

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 23期

关键词：

macrocyclic hydrogen bonding receptor; chiral recognition; hydroxyacids; spirobifluorene; chromenone;

D O I：

10.1016/S0040-4039(00)00693-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Good chiral recognition of hydroxycarboxylates such as lactic or mandelic acids has been achieved with a macrocyclic receptor, readily available from a known bis-chromenylurea and a spirobifluorene linker. Resolution of the receptor racemic mixture was carried out taking advantage of its complexing properties with (R)-mandelic acid tetramethylammonium salt on a TLC plate. (C) 2000 Elsevier Science Ltd, All rights reserved.

引用

页码：4563 / 4566

页数：4

共 18 条

[1] ENANTIOSELECTIVE COMPLEXATION OF CHIRAL DICARBOXYLIC-ACIDS IN CLEFTS OF FUNCTIONALIZED 9,9'-SPIROBIFLUORENES [J].

ALCAZAR, V ;

DIEDERICH, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (11) :1521-1523

[2]

ALCAZAR V, 1991, TETRAHEDRON LETT, V32, P5309

[3] Chiral recognition of lactic acid derivatives with chromenone-benzoxazole receptors [J].

Almaraz, M ;

Raposo, C ;

Martín, M ;

Caballero, MC ;

Morán, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (14) :3516-3517

[4] MOLECULAR CLEFTS DERIVED FROM 9,9'-SPIROBI[9H-FLUORENE] FOR ENANTIOSELECTIVE COMPLEXATION OF PYRANOSIDES AND DICARBOXYLIC-ACIDS [J].

CUNTZE, J ;

OWENS, L ;

ALCAZAR, V ;

SEILER, P ;

DIEDERICH, F .

HELVETICA CHIMICA ACTA, 1995, 78 (02) :367-390

[5] Carbohydrate recognition: Enantioselective spirobifluorene diphosphonate receptors [J].

Das, G ;

Hamilton, AD .

TETRAHEDRON LETTERS, 1997, 38 (21) :3675-3678

[6] Receptors for carboxylates derived from 2-furoic and fusaric acids [J].

delaTorre, MF ;

Gonzalez, S ;

Campos, EG ;

Mussons, ML ;

Moran, JR ;

Caballero, MC .

TETRAHEDRON LETTERS, 1997, 38 (49) :8591-8594

[7] OPTICALLY ACTIVE 9,9'-SPIROBIFLUORENE DERIVATIVES [J].

HAAS, G ;

PRELOG, V .

HELVETICA CHIMICA ACTA, 1969, 52 (05) :1202-&

[8] Chiral recognition of tartaric acid derivatives with chromenone-benzoxazole receptors and a spirobifluorene spacer [J].

Hernández, JV ;

Almaraz, M ;

Raposo, C ;

Martín, M ;

Lithgow, A ;

Crego, M ;

Caballero, C ;

Morán, JR .

TETRAHEDRON LETTERS, 1998, 39 (40) :7401-7404

[9] OPTICAL-ACTIVITY OF CHROMOPHORES OF SYMMETRY C2 [J].

HUG, W ;

WAGNIERE, G .

TETRAHEDRON, 1972, 28 (05) :1241-&

[10] Efficient recognition of chiral carbamoyl-alpha-hydroxyacids with a cleft-type receptor [J].

Martin, M ;

Raposo, C ;

Almaraz, M ;

Crego, M ;

Caballero, C ;

Grande, M ;

Moran, JR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (20) :2386-2388

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