Preparation of Binaphthyldiamine Derived Chiral Stationary Phases

Abstract

1,1'-Binaphthyl-2,2'-diamine and its derivatives have been used as a very powerful chiral catalyst for asymmetric synthesis. The preparative separation of racemic 1,1'binaphthyl-2,2'-diamine has been reported recently, but very few results by using this compound as a chiral selector have been reported. Miyano and co-workers reported on the many uses of chiral binaphthalene derivatives as a chiral derivatizing agent, a chiral catalyst, and chiral stationary phases. (CSPs) In their work, the CSPs were prepared with binaphthyl dicarboxylic acids and the separated samples were limited to the derivatives of few chiral compounds as the overall selectivity was not good. Uray et al. also reported on the use of diphenylethanediamine derivatives, including 3,5-dinitrobenzoyl group, as chiral selectors, and tried to separate different enantiomeric compounds. He succeeded in separating some derivatized chiral compound and a few underivatized chiral samples with generally low selectivity levels. In this study, we report on the preparation of four different 1,1'-binaphthyl-2,2'-diamine derived chiral stationary phases (CSPs 1-4), and showed the separation results of randomly selected commercially available chiral compounds on these columns.