Simultaneous enantioresolution and assignment of absolute configuration of secondary alcohols by directly coupled HPLC-NMR of 9-AMA esters

被引：27

作者：

Seco, JM

Tseng, LH

Godejohann, M

Quiñoá, E

Riguera, R ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Fac Quim, Dept Quim Organ, E-15706 Santiago De Compostela, Spain

[2] Univ Santiago de Compostela, Inst Acuicultura, E-15706 Santiago De Compostela, Spain

[3] Bruker Biospin GmbH, D-76287 Rheinstetten, Germany

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 19期

关键词：

D O I：

10.1016/S0957-4166(02)00510-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Derivatization of mixtures of enantiomers (including racemates) of chiral secondary alcohols with a pure enantiomer of the auxiliary reagent, 9-anthrylmethoxyacetic acid [(R)- or (S)-9-AMA)] followed by directly coupled HPLC-NMR of the mixture of the esters allows separation of the two enantiomers, the determination of the e.e. and the assignment of their absolute configuration in a single operation and with just a few micrograms of substance. The procedure can also be applied to the assignment of the absolute configuration of a single enantiomer of the alcohol. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：2149 / 2153

页数：5

相关论文

共 16 条

[1] HPLC-NMR on-line coupling including the ROESY technique:: Direct characterization of naphthylisoquinoline alkaloids in crude plant extracts [J].

Bringmann, G ;

Günther, C ;

Schlauer, J ;

Rückert, M .

ANALYTICAL CHEMISTRY, 1998, 70 (14) :2805-2811

[2] Combined HPLC-MS and HPLC-NMR on-line coupling for the separation and determination of lutein and zeaxanthin stereoisomers in spinach and in retina [J].

Dachtler, M ;

Glaser, T ;

Kohler, K ;

Albert, K .

ANALYTICAL CHEMISTRY, 2001, 73 (03) :667-674

[3]

Eliel E. L., 1994, STEREOCHEMISTRY ORGA, P214

[4] The use of ethyl 2-(9-anthryl)-2-hydroxyacetate for assignment of the absolute configuration of carboxylic acids by H-1 NMR [J].

Ferreiro, MJ ;

Latypov, SK ;

Quinoa, E ;

Riguera, R .

TETRAHEDRON-ASYMMETRY, 1997, 8 (07) :1015-1018

[5] Assignment of the absolute configuration of α-chiral carboxylic acids by 1H NMR spectroscopy [J].

Ferreiro, MJ ;

Latypov, SK ;

Quiñoá, E ;

Riguera, R .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (09) :2658-2666

[6] Determination of the absolute configuration and enantiomeric purity of chiral primary alcohols by H-1 NMR of 9-anthrylmethoxyacetates. [J].

Ferreiro, MJ ;

Latypov, SK ;

Quinoa, E ;

Riguera, R .

TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2195-2198

[7] CONFORMATIONAL STRUCTURE AND DYNAMICS OF ARYLMETHOXYACETATES - DNMR SPECTROSCOPY AND AROMATIC SHIELDING EFFECT [J].

LATYPOV, SK ;

SECO, JM ;

QUINOA, E ;

RIGUERA, R .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :504-515

[8] Assignment of the absolute configuration of β-chiral primary alcohols by NMR:: Scope and limitations [J].

Latypov, SK ;

Ferreiro, MJ ;

Quiñoá, E ;

Riguera, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4741-4751

[9] Directly coupled HPLC-NMR and HPLC-NMR-MS in pharmaceutical research and development [J].

Lindon, JC ;

Nicholson, JK ;

Wilson, ID .

JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2000, 748 (01) :233-258

[10] Determining factors in the assignment of the absolute configuration of alcohols by NMR. The use of anisotropic effects on remote positions. [J].

Seco, JM ;

Latypov, SK ;

Quinoa, E ;

Riguera, R .

TETRAHEDRON, 1997, 53 (25) :8541-8564