Enantiopure O-Ethyl Phenylphosphonothioic Acid: A Solvating Agent for the Determination of Enantiomeric Excesses

被引：3

作者：

Matsumoto, Kazushige ^{[1
]}

Sawayama, Jun ^{[1
]}

Hirao, Shotaro ^{[1
]}

Nishiwaki, Nagatoshi ^{[1
]}

Sugimoto, Ryuichi ^{[1
]}

Saigo, Kazuhiko ^{[1
]}

机构：

[1] Kochi Univ Technol, Sch Environm Sci & Engn, Kami, Koch 7828502, Japan

来源：

CHIRALITY | 2014年 / 26卷 / 10期

关键词：

amine; amino alcohol; alcohol; H-1 NMR analysis; enantioseparation; diastereomeric salt formation; T-BUTYLPHENYLPHOSPHINOTHIOIC ACID; CHIRAL RECOGNITION ABILITY; ABSOLUTE-CONFIGURATION; NMR; PHOSPHORUS; ASSIGNMENT; MECHANISM; PURITY;

D O I：

10.1002/chir.22315

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An improved method, which is highly reproducible, was developed for the enantioseparation of racemic O-ethyl phenylphosphonothioic acid (1a) with brucine by introducing seeding to a supersaturated solution of the diastereomeric salt mixture. The present method gave both diastereomeric salts in high yields with a diastereomeric ratio of >99.5:0.5 upon choosing the crystallization solvent (MeOH for the (R)-1a salt and MeOH/H2O for the (S)-1a salt). The enantiopure acid 1a showed a good chirality recognition ability for not only strong bases, such as amines and amino alcohols, but also weakly basic alcohols and was applicable as a solvating agent to the H-1 NMR determination of the enantiomeric excess of chiral amines, amino alcohols, and alcohols, including aliphatic substrates. (C) 2014 Wiley Periodicals, Inc.

引用

页码：614 / 619

页数：6

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