Stereochemical study on planar‐chiral cyclic molecules using polysaccharide‐based column chromatography
Stereochemical study on planar‐chiral cyclic molecules using polysaccharide‐based column chromatography
复制标题
使用多糖柱色谱法研究平面手性环状分子的立体化学
DOI：
10.1002/chir.23429
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发表时间：
2022
期刊：
影响因子：
2
通讯作者：
Tomooka Katsuhiko
中科院分区：
文献类型：
--
作者：
Igawa Kazunobu;Uehara Kazuhiro;Kawasaki Yuuya;Tomooka Katsuhiko
通过分析型高效液相色谱法（HPLC）观察可分离的对映异构体，揭示了各种中等大小杂环（沿着九元环酮及其烯醇酯）的平面手性的存在，该色谱法使用带有基于多糖的手性选择剂的手性固定相。通过制备级HPLC成功分离了数十毫克平面手性分子的对映体，从而制备了对映体富集的样品。这反过来又使详细的立体化学研究成为可能，包括测量光学活性的半衰期和X射线晶体学以阐明立体化学。
The presence of planar chirality of a variety of medium‐sized heterocycles, along with nine‐membered cyclic ketone and its enol ester, was revealed by observation of isolable enantiomers by analytical high‐performance liquid chromatography (HPLC) using a chiral stationary phase with a polysaccharide‐based chiral selector. Several tens of milligrams of enantiomers of the planar‐chiral molecules were successfully separated by preparative‐scale HPLC, leading to the preparation of an enantioenriched sample. This in turn enabled detailed stereochemical studies, including measurement of half‐lives of the optical activity and X‐ray crystallography for elucidation of stereochemistry.