Kodama Koichi, Takase Fusato, Hirose Takuji
Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University Japan
RSC Adv. 2021 May 19;11(30):18162-18170. doi: 10.1039/d1ra03546k.
Amidine-based optically active resolving agents for enantiomer separation of axially chiral 1,1'-biaryl-2,2'-diols have been developed. A strongly basic amidine bearing no substituents on its nitrogen atoms enables the formation of their diastereomeric salts upon being mixed with weakly acidic phenol derivatives. Enantiopure 1,1'-biaryl-2,2'-diols can be obtained in high yields after only one crystallization of their salts with the chiral amidine derived from dehydroabietic acid. X-ray crystallography revealed that the amidine moiety forms a salt with the phenol group and additional intermolecular NH/π interactions contribute to the efficient chiral recognition process.
已开发出用于轴向手性1,1'-联芳基-2,2'-二醇对映体分离的基于脒的旋光拆分剂。在其氮原子上没有取代基的强碱性脒与弱酸性酚衍生物混合时能够形成非对映体盐。仅将其盐与脱氢枞酸衍生的手性脒进行一次结晶后，就能以高收率获得对映体纯的1,1'-联芳基-2,2'-二醇。X射线晶体学表明，脒部分与酚基团形成盐，额外的分子间NH/π相互作用有助于高效的手性识别过程。
