Enantioseparation of racemic N-acylarylalkylamines on various amino alcohol derived tau-acidic chiral stationary phases.
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.
Ryoo
Jae Jeong
JJ
Department of Chemistry, Graduate School, Kyungpook National University, 1370 Sankyuk-Dong, Buk-Ku, Taegu 702-701, South Korea. jjryoo@knu.ac.kr
Kim
Tae Hyuk
TH
Im
Sung Hyun
SH
Jeong
Young Han
YH
Park
Ji Yeon
JY
Choi
Seong-Ho
SH
Lee
Kwang-Pill
KP
Park
Jung Hag
JH
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
D000588:Amines; D000605:Amino Alcohols