Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine via diastereomeric salt formation.
Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine via diastereomeric salt formation.
复制标题
通过非对映体盐形成 1-苯乙胺对映体分离中溶剂诱导的手性控制。
作者：
K. Kodama;Yuria Kimura;Hiroaki Shitara;M. Yasutake;R. Sakurai;T. Hirose
研究了溶剂诱导手性控制在N-（对甲苯磺酰基）-（S）-苯丙氨酸2与1-苯乙胺1形成非对映体盐拆分中的应用。(S)-1·（S）-2优先从醇水溶液中结晶为较难溶的盐，而（R）-1·（S）-2盐主要通过将具有六元环的溶剂如二氧六环、环己烷、四氢吡喃和环己烯加成到2-丙醇中获得。从分子结构、旋光度测量和X射线晶体学分析的角度进行了进一步的研究。晶体学分析表明，在（R）-1·（S）-2中引入无氢键的六元环溶剂分子改变了（S）-2的分子构象，使盐稳定，从而改变了1在对映体分离中的选择性。
Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine 1 by N-(p-toluenesulfonyl)-(S)-phenylalanine 2 via diastereomeric salt formation was studied. (S)-1·(S)-2 was preferentially crystallized as a less-soluble salt from aqueous alcohol, while (R)-1·(S)-2 salt was mainly obtained by addition of solvents with a six-membered ring such as dioxane, cyclohexane, tetrahydropyran, and cyclohexene to 2-propanol. Further investigations were carried out from the viewpoints of molecular structures, optical rotation measurement, and X-ray crystallographic analyses. Crystallographic analyses have revealed that incorporation of the six-membered ring solvent molecule in (R)-1·(S)-2 without hydrogen bonds changed the molecular conformation of (S)-2 to stabilize the salt, which changed the selectivity of 1 in the enantioseparation.
CH/π 相互作用在难溶性非对映盐晶体稳定中的作用
DOI：
--
发表时间：
2007
期刊：
The Chemical Record 7
影响因子：
--
作者：
Saigo;K.;Kobayashi;Y.
通讯作者：
Y.
影响因子：
4.3
作者：
Kodama, Koichi;Kobayashi, Yuka;Saigo, Kazuhiko
通讯作者：
Saigo, Kazuhiko