Enantioseparation of racemic N-acylarylalkylamines on various amino alcohol derived π-acidic chiral stationary phases

Jae Jeong Ryoo; Tae Hyuk Kim; Sung Hyun Im; Young Han Jeong; Ji Yeon Park; Seong Ho Choi; Kwang Pill Lee; Jung Hag Park

doi:10.1016/S0021-9673(02)01702-8

Enantioseparation of racemic N-acylarylalkylamines on various amino alcohol derived π-acidic chiral stationary phases

Jae Jeong Ryoo, Tae Hyuk Kim, Sung Hyun Im, Young Han Jeong, Ji Yeon Park, Seong Ho Choi, Kwang Pill Lee, Jung Hag Park

Department of Chemical Science Education

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

Five π-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.

Original language	English
Pages (from-to)	429-438
Number of pages	10
Journal	Journal of Chromatography A
Volume	987
Issue number	1-2
DOIs	https://doi.org/10.1016/S0021-9673(02)01702-8
State	Published - 14 Feb 2003

Keywords

Acylarylalkylamines
Alkylamines
Amines
Chiral stationary phases, LC
Enantiomer separation

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10.1016/S0021-9673(02)01702-8

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title = "Enantioseparation of racemic N-acylarylalkylamines on various amino alcohol derived π-acidic chiral stationary phases",

abstract = "Five π-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.",

keywords = "Acylarylalkylamines, Alkylamines, Amines, Chiral stationary phases, LC, Enantiomer separation",

author = "Ryoo, {Jae Jeong} and Kim, {Tae Hyuk} and Im, {Sung Hyun} and Jeong, {Young Han} and Park, {Ji Yeon} and Choi, {Seong Ho} and Lee, {Kwang Pill} and Park, {Jung Hag}",

year = "2003",

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doi = "10.1016/S0021-9673(02)01702-8",

language = "English",

volume = "987",

pages = "429--438",

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T1 - Enantioseparation of racemic N-acylarylalkylamines on various amino alcohol derived π-acidic chiral stationary phases

AU - Ryoo, Jae Jeong

AU - Kim, Tae Hyuk

AU - Im, Sung Hyun

AU - Jeong, Young Han

AU - Park, Ji Yeon

AU - Choi, Seong Ho

AU - Lee, Kwang Pill

AU - Park, Jung Hag

PY - 2003/2/14

Y1 - 2003/2/14

N2 - Five π-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.

AB - Five π-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.

KW - Acylarylalkylamines

KW - Alkylamines

KW - Amines

KW - Chiral stationary phases, LC

KW - Enantiomer separation

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U2 - 10.1016/S0021-9673(02)01702-8

DO - 10.1016/S0021-9673(02)01702-8

M3 - Article

C2 - 12613838

AN - SCOPUS:0037435959

SN - 0021-9673

VL - 987

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EP - 438

JO - Journal of Chromatography A

JF - Journal of Chromatography A

IS - 1-2

ER -

Enantioseparation of racemic N-acylarylalkylamines on various amino alcohol derived π-acidic chiral stationary phases

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