Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved Materials

Article abstract of DOI:10.1021/jo00098a038

Racemic 2,2'-dihydroxy-1,1'-binaphyl and 10,10'-dihydroxy-9,9'-biphenanthryl have been resolved effectively by crystalline complexation with commercially available N-alkylcinchonidium halides.The resolved complexes were studied by X-ray diffraction methods in order to characterize the intermolecular interaction and recognition schemes.The results indicate the significance of directional hydrogen bonding and aryl-aryl interaction modes in the molecular recognition process.