Optical Resolution of 2'-Methoxy-1,1'-binaphthyl-2-carboxylic Acid, and Application to Chiral Derivatizing Agent for HPLC Separation of Enantiomeric Alcohols and Amines

Article abstract of DOI:10.1246/bcsj.62.1528

Racemic 2'-methoxy-1,1'-binaphthyl-2-carboxylic acid was separated on a multi-gram scale into its antipodes via silica-gel column chromatography followed by alkine hydrolysis of the diastereomeric esters prepared from (R)-1-phenylethanol or (-)-menthol.The molecular structure of (-)-menthyl (aS)-2'-methoxy-1,1'-binaphthyl-2-carboxylate was determined by single-crystal X-ray analysis.The (aS)-acid was converted to crystalline acid chloride, which was conveniently utilized as efficient chiral derivatizing agent for differentiation of enantiomeric alcohols and amines by high-performance liquid chromatography on silica gel.The elution behavior of a pair of diastereomeric esters or amides was explained by the steric interactions between the solutes and the silica-gel stationary phase on the basis of the X-ray analysis.