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

Jeongjae Yu; Jung Mi Lee; Jae Jeong Ryoo

doi:10.1002/chir.22576

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

Jeongjae Yu, Jung Mi Lee, Jae Jeong Ryoo

Department of Chemical Science Education

Kyungpook National University

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

8 Scopus citations

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.

Original language	English
Pages (from-to)	276-281
Number of pages	6
Journal	Chirality
Volume	28
Issue number	4
DOIs	https://doi.org/10.1002/chir.22576
State	Published - 1 Apr 2016

Keywords

(R)-phenylglycinol
(S)-leucinol
adamantyl-derived CSP
chiral stationary phase
different acid chlorides

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10.1002/chir.22576

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title = "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.",

keywords = "(R)-phenylglycinol, (S)-leucinol, adamantyl-derived CSP, chiral stationary phase, different acid chlorides",

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T1 - Chiral separation on various modified amino alcohol-derived HPLC chiral stationary phases

AU - Yu, Jeongjae

AU - Lee, Jung Mi

AU - Ryoo, Jae Jeong

PY - 2016/4/1

Y1 - 2016/4/1

N2 - 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.

AB - 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.

KW - (R)-phenylglycinol

KW - (S)-leucinol

KW - adamantyl-derived CSP

KW - chiral stationary phase

KW - different acid chlorides

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U2 - 10.1002/chir.22576

DO - 10.1002/chir.22576

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SN - 0899-0042

VL - 28

SP - 276

EP - 281

JO - Chirality

JF - Chirality

IS - 4

ER -

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

Abstract

Keywords

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