Development of a method for preparation of optically active compounds under thermodynamical equilibrium conditions based on inclusion complexation

以间溴苯甲醚为原料，经4步反应合成了外消旋体2，7，10，15-四羟基四苯撑（THTP），总收率45%。通过与（S）-苯乙胺的包合反应实现了外消旋THTP的光学拆分，得到了（-）-THTP，可作为外消旋苯乙胺光学拆分为（S）-苯乙胺的主体分子。X射线晶体学研究表明，主体分子THTP巧妙地通过氢键和货车德瓦尔斯相互作用包含客体分子。包合物由（-）-THTP、（S）-苯乙胺和甲苯按1：2：1的比例组成。

Racemic 2,7,10,15-tetrahydroxytetraphenylene (THTP) was synthesized starting from 3-bromoanisole in 4 steps (overall yield 45%). Optical resolution of the racemic THTP was achieved by include complexation using (S)-phenethylamine to afford (-)-THTP, which could be used as a host molecule for optical resolution of racemic phenethylamine to (S)-phenethylamine. An X-ray crystallographic study elucidated that the host molecules THTP ingeniously included the guest molecule via hydrogen bonding and van der Waals interactions. Furthermore, the inclusion complex consisted of (-)-THTP, (S)-phenethylamine, and toluene in a 1 : 2 : 1 ratio, respectively.