Enantiopure O-Ethyl Phenylphosphonothioic Acid: A Solvating Agent for the Determination of Enantiomeric Excesses
Enantiopure O-Ethyl Phenylphosphonothioic Acid: A Solvating Agent for the Determination of Enantiomeric Excesses
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对映体纯 O-乙基苯基硫代膦酸：用于测定对映体过量的溶剂
DOI：
10.1002/chir.22315
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发表时间：
2014
期刊：
影响因子：
2
通讯作者：
and Kazuhiko Saigo
中科院分区：
文献类型：
--
作者：
Kazushige Matsumoto;Jun Sawayama;Shotaro Hirao;Nagatoshi Nishiwaki;Ryuichi Sugimoto;and Kazuhiko Saigo
通过在非对映异构体盐混合物的过饱和溶液中引入种子，建立了一种重复性高的改进方法，用于外消旋ico -乙基苯基膦硫代酸（1a）与马钱子碱的对映分离。本方法在选择结晶溶剂(（R)-1盐为MeOH， (S)-1盐为MeOH/H2O）的条件下，获得了两种非对映异构体盐的高收率，非对映异构体比为>99.5:0.5。对映纯酸(R)-1a、(S)-1不仅对胺、氨基醇等强碱，而且对弱碱性醇也表现出良好的手性识别能力，可作为溶剂剂应用于手性胺、氨基醇、醇（包括脂肪族底物）对映体过量的1h NMR测定。手性，2014,26(6):614 - 619。©2014 Wiley期刊公司
An improved method, which is highly reproducible, was developed for the enantioseparation of racemicO‐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)-1asalt and MeOH/H2O for the ((S)-1asalt). The enantiopure acid(R)-1a,(S)-1ashowed 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 the1H NMR determination of the enantiomeric excess of chiral amines, amino alcohols, and alcohols, including aliphatic substrates.Chirality 26:614–619, 2014. © 2014 Wiley Periodicals, Inc.