Enantiomeric Resolution of ¥á-Amino Acid Derivatives on Two Diastereomeric Chiral Stationary Phases Based on Chiral Crown Ethers Incorporating Two Different Chiral Units

Bulletin of the Korean chemical society

Myung Ho Hyun¹  Hee Jung Choi¹  Yoon Jae Cho¹  Hee Jin Kim¹ 

关键词: Chiral stationary phase;    Enantiomeric resolution;    Liquid chromatography;    ¥á-Amino acid derivatives;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

Two diastereomeric chiral stationary phases (CSPs) were applied to the liquid chromatographic resolution of various racemic �?-amino methyl esters, �?-amino N,N-diethylamides and �?-amino N-propylamides. The CSP incorporating (R)- 3,3�?-diphenyl-1,1�?-binaphtyl and (R,R)-tartaric acid unit as chiral barriers did not show any chiral recognition. In contrast, the CSP incorporating (R)-3,3�?-diphenyl-1,1�?-binaphtyl and (S,S)-tartaric acid unit as chiral barriers was found to show excellent chiral recognition especially for the two enantiomers of �?-amino N-propylamides. Some of �?-amino methyl esters and �?-amino N,N-diethylamides were also resolved on the CSP incorporating (R)-3,3�?-diphenyl-1,1�?- binaphtyl and (S,S)-tartaric acid unit. From these results it was concluded that the two chiral units composing the diastereomeric CSPs can show “matched�? or “mismatched�? effect on the chiral recognition according to their absolute stereochemistry.

【 授权许可】

Unknown