title: Enantioseparation of racemic N-acylarylalkylamines on various amino alcohol derived tau-acidic chiral stationary phases.
abstract: Five tau-acidic chiral stationary phases (CSPs), CSP 4, CSP 5, CSP 6, CSP 7 and CSP 8, were prepared by connecting the N-(3,5-dimethylbenzoyl) derivative of (R)-alaninol, (S)-leucinol, (1S,2R)-ephedrine and (S)-tert-leucinol and the O-(3,5-dinitrobenzoyl) derivative of (R)-phenylglycinol to silica gel through a carbamate or urea linkage. The CSPs were applied to the resolution of various racemic N-acyl-1-naphthylaminoalkanes by chiral HPLC, and the chromatographic resolution results were compared with those of previously reported CSPs (CSP 2, CSP 3), which are derived from N-(3,5-dinitrobenzoyl)-(1S,2R)-norephedrine and N-(3,5-dinitrobenzoyl-(R)-phenylglycinol. Based on a comparison of the resolution results for each CSP, the role of each functional group on the five chiral selectors is explained.
authors.affiliation: Department of Chemistry, Graduate School, Kyungpook National University, 1370 Sankyuk-Dong, Buk-Ku, Taegu 702-701, South Korea. jjryoo@knu.ac.kr
authors.forename: Jae Jeong
authors.initials: JJ
authors.lastname: Ryoo
authors.forename: Tae Hyuk
authors.initials: TH
authors.lastname: Kim
authors.forename: Sung Hyun
authors.initials: SH
authors.lastname: Im
authors.forename: Young Han
authors.initials: YH
authors.lastname: Jeong
authors.forename: Ji Yeon
authors.initials: JY
authors.lastname: Park
authors.forename: Seong-Ho
authors.initials: SH
authors.lastname: Choi
authors.forename: Kwang-Pill
authors.initials: KP
authors.lastname: Lee
authors.forename: Jung Hag
authors.initials: JH
authors.lastname: Park
mesh_terms: D000588:Amines / Q000737:chemistry / Q000302:isolation & purification*; D000605:Amino Alcohols / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: D000588:Amines; D000605:Amino Alcohols