Chiral separation on various modified amino alcohol‐derived HPLC chiral stationary phases

Abstract

3,5-Dinitrobenzoyl chloride was previously used for the preparation of (R)-phenylglycinol- and (S)-leucinol-derived chiral stationary phases. In this study, 3,5-bis(trifluoromethyl)benzoyl chloride, 2-furoyl chloride, 2-theonyl chloride, 10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride, diphenylcarbamoyl chloride, and 1-adamantanecarbonyl chloride were used to prepare six new phenylglycinol-derived chiral stationary phases (CSPs) and five new leucinol-derived CSPs. Using these 11 CSPs, chiral separation of nine π-acidic amino acid derivatives and five π-basic compounds was performed, and the separation results were compared. An adamantyl-derived CSP showed good separation.

Synthesis and application of N‐3,5‐dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

“…The synthetic procedures for CSP 1, CSP 2, and CSP 3 are shown in Scheme 1 and those of CSP 4, CSP 5, and CSP 6 are shown in Scheme 2. CSP 1, CSP 2, and CSP 3 were prepared using a previously reported method 9,10 . Most of the syntheses of CSP 4, CSP 5, and CSP 6 was followed by a recent paper in our lab, 11,12 but by using pyridine as a solvent, the reaction time was shortened and the efficiency of attaching the chiral selector (silane compound) to silica was improved.…”

“…Forty-four chiral samples were used in this study. Samples were classified into three groups for convenience: Group A consists of 12 π-acidic amino acid derivatives which were prepared by our group, [9][10][11][12]17 group B consists of 13 commercially available π-basic samples purchased from Sigma-Aldrich Korea (Seoul, Korea), and group C consists of 19 oxazolidinone series chiral antibiotics which were obtained from Prof. Armstrong's Lab (UTA, Texas, USA). About 5-10 mg of each sample and 1-2 mg of TTBB were dissolved in 5 ml of dichloromethane to check dead time.…”

“…Various types of high‐performance liquid chromatography (HPLC) chiral stationary phases (CSPs), such as Brush/Pirkle‐type, 1 ligand exchange, 2 crown ether, 3 protein, 4 polysaccaride, 5 cyclodextrin, 6 and cyclofructan 7 CSPs, have been developed 8 . Recently, a (R)‐phenylglycinol derived C 3 symmetry CSP and three C 2 symmetric CSPs were prepared and compared with a N ‐3,5‐dintrobenzoyl (DNB)‐(R)‐phenylglycinol derived CSP, which was previously reported as a Brush/Pirkle‐type CSP 9,10 for various chiral samples under the same separation conditions 11,12 . As a result, the (R)‐phenylglycinol C 3 symmetry CSP showed better resolution and recognized more chiral samples than others 11,12 …”

Amino alcohol‐derived chiral stationary phases

“…[69][70][71][72][73][74][75][76][77][78][79][80][81] The α-amino alcohol-based CSPs have been frequently reported in chiral separation without the use of the ligand exchange mode. 67,[82][83][84][85][86][87][88][89] First, Pirkle-type π-acidic CSP prepared by our group, based on an α-amino alcohol, was an (R)-phenylglycinol 3,5-dinitrobenzoyl derived CSP. 82 Thereafter, starting materials such as the (S)-leucinol, (S)alaninol, (1S,2R)-norephedrine, (1S,2R)-ephedrine, and (S)-tert-leucinol were used to prepare amino alcohol-based 3,5-dinitrobenzoyl-derived CSPs.…”

Enantioseparation on Amino Alcohol‐Derived Stationary Phases by Supercritical Fluid Chromatography and High‐Performance Liquid Chromatograpy

“…In this study, we examined the effect of the mobile phase composition and the particle size of silica gel on the resolution using a chiral selector developed in our lab 14 . Chiral separation was performed by high‐performance liquid chromatograpy (HPLC) and SFC, and the results were compared to each other.…”