A Novel Application of Cinchona Alkaloids as Chiral Auxiliares: Preparation and Use of a New Family of Chiral Stationary Phases for the Chromatographic Resolution of Racemates

The preparation of new chiral stationary phases derived from quinine, quinidine and cinchonidine and their application to resolution of racemic binaphthyl derivatives are described. From the comparison of the results achieved on the three phases, the knowledge of the elution orders, obtained by circular dichroism, and the analysis, by 'H NMR spectroscopy, of the structures of the adducts between quinine and 2'-(2-propoxyj- l,l'-binaphthyl-2-01, it has been possible to provide an experimental basis to a chiral recognition mechanism.