Practical enantioresolution of alcohols with 2-methoxy-2-(1-naphthyl)propionic acid and determination of their absolute configurations by the 1H NMR anisotropy method

被引：53

作者：

Taji, H

Kasai, Y

Sugio, A

Kuwahara, S

Watanabe, M

Harada, N

Ichikawa, A

机构：

[1] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Aoba Ku, Sendai, Miyagi 9808577, Japan

[2] Natl Inst Agrobiol Sci, Ibaraki, Osaka, Japan

来源：

CHIRALITY | 2002年 / 14卷 / 01期

关键词：

racemic; 2-alkanols; 1-octyn-3-ol; diastereomeric mixtures; HPLC separation on silica gel; enantiopure alcohols;

D O I：

10.1002/chir.10038

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The enantioresolution of racemic alcohols as esters of 2-methoxy-2-(1-naphthyl)propionic acid (M alpha NP acid 1) and the determination of their absolute configurations on the basis of H-1 NMR anisotropy effect are described. The enantiopure M alpha NP acid (S)-(+)-1 was allowed to react with racemic 2-alkanols and 1-octyn-3-ol, yielding diastereomeric mixtures of esters, which were easily separated by HPLC on silica gel. To determine the absolute configurations of the first-eluted diastereomeric esters by the H-1 NMR anisotropy method, the general scheme was proposed. Separated esters were reduced with LiAlH4 or hydrolyzed with KOH/EtOH to recover enantiopure alcohols. (C) 2002 Wiley-Liss, Inc.

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页码：81 / 84

页数：4

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