Liao Jian, Peng Xiaohua, Zhang Juhua, Yu Kaibei, Cui Xin, Zhu Jin, Deng Jingen
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.
Org Biomol Chem. 2003 Mar 21;1(6):1080-5. doi: 10.1039/b211327a.
An effective resolving agent, (2S, 3S)-di-O-(p-toluoyl) tartaric acid(4), was screened using a 'family' approach to yield direct resolution of (R)-terbutaline (1) with high optical purity and yield. Molecular recognition was studied by X-ray crystallographic analyses of the single crystals of the pair of diastereomeric salts. The more-soluble salt formed a sheet supramolecular structure, and the less-soluble salt formed a columnar supramolecular structure by enantiodifferentiating self-assembly. The water molecule plays an important role during optical resolution, and makes the supramolecular structure of the less-soluble salt more thermodynamically stable than that of the more-soluble salt. Solvent system has little influence on the resolution.
使用“家族”方法筛选出一种有效的拆分剂（2S，3S）-二-O-（对甲苯甲酰基）酒石酸（4），以直接拆分获得高光学纯度和产率的（R）-特布他林（1）。通过对这对对映体盐单晶的X射线晶体学分析研究了分子识别。溶解度较大的盐形成片状超分子结构，而溶解度较小的盐通过对映体选择性自组装形成柱状超分子结构。水分子在光学拆分过程中起重要作用，使溶解度较小的盐的超分子结构比溶解度较大的盐的超分子结构在热力学上更稳定。溶剂体系对拆分影响很小。
