title: Facile resolution of racemic terbutaline and a study of molecular recognition through chiral supramolecules based on enantiodifferentiating self-assembly.
abstract: 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.
authors.affiliation: Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.
authors.forename: Jian
authors.initials: J
authors.lastname: Liao
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Peng
authors.forename: Juhua
authors.initials: J
authors.lastname: Zhang
authors.forename: Kaibei
authors.initials: K
authors.lastname: Yu
authors.forename: Xin
authors.initials: X
authors.lastname: Cui
authors.forename: Jin
authors.initials: J
authors.lastname: Zhu
authors.forename: Jingen
authors.initials: J
authors.lastname: Deng