A highly efficient and practical resolution of racemic 1,1′-bi-2-naphthol (BINOL) has been achieved through molecular complexation with N-benzylcinchoninium chloride, which can be readily prepared in 85% yield using an improved procedure through the reaction of cinchonine with benzyl chloride in dimethylformamide (DMF). It is found that the absolute configuration of BINOL included in the molecular crystals is R, which is the same as in the case of using N-benzylcinchonidinium chloride. This result is discussed in terms of molecular recognition in the solid state. X-Ray structural analysis of molecular crystal formed between (R)-BINOL and N-benzylcinchoninium chloride indicates that the additive effect of the chiral features of the host, the interaction pattern between the functional groups of the host and guest, and the complementary molecular packing in the crystal lattice dominates the stereochemistry of the guest in the molecular crystal.

中文翻译：

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N-苄基金鸡顿碱分子络合用于双酚光学拆分的实用方法和新机理

通过与N-苄基金鸡顿鎓氯化物进行分子络合，已经获得了高效，实用的外消旋1,1'-联-2-萘酚（BINOL）拆分方法，该方法可以通过改进的方法通过与N-苄基金鸡顿铵反应而轻松制备，产率为85％。辛可宁与二甲基甲酰胺（DMF）中的苄基氯。发现分子晶体中所包含的BINOL的绝对构型为R，其与使用N-苄基钦可丁鎓氯化物的情况相同。从固态分子识别的角度讨论了这一结果。（R）-BINOL与N之间形成的分子晶体的X射线结构分析-苄基金鸡铵盐表明，主体的手性特征的加性效应，主体与客体的官能团之间的相互作用模式以及晶格中的互补分子堆积控制了客体在分子晶体中的立体化学。