Preparation of New Binaphthol Derived Chiral Stationary Phases

Abstract

To develop more advanced binaphthol derived CSPs, two new 1,1-bi-2-naphthol derived chiral stationary phases (CSPs) (CSP 1 and CSP 2) were prepared by connecting with silica gel at a hydroxy (OH) group of binaphthol. Previously reported two 1,1'-binaphthyl-2,2'-diamine derived CSPs (CSP 3 and CSP 4) were also prepared to compare the role of their functional groups (-OH and -NH2) with CSP 1 and CSP 2. Enantioseparation of randomly selected, 11 chiral compounds on these four CSPs was performed and the results compared to each other. 3,5-Dinitrobenzoyl (3,5-DNB) derivatives of each CSP showed better results than the others and binaphthyldiamine derived CSP showed slightly better than binaphthol derived one.

Preparation of Bonded Cellulose Tris(3,5-dimethylphenylcarbamate) Chiral Stationary Phases by Using Three Bifunctional Reagents

“…The resulting CSP 1-3 were suspended in a hexane/IPA (90/10, v/v) mixture and packed in a stainless steel column (25 cm long with an internal diameter of 0.46 cm) at 7000 psi using a slurry packing method, respectively. 18,19 The resulting packed columns were used in the subsequent HPLC experiments.…”