Enantiomeric separations of α-aryl ketones with cyclofructan chiral stationary phases via high performance liquid chromatography and supercritical fluid chromatography

Anthony S. Breitbach, Yeeun Lim, Qing Long Xu, László Kürti, Daniel W. Armstrong, Zachary S. Breitbach

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

Normal phase chiral HPLC and SFC methods are presented for the enantiomeric separation of 21 α-aryl ketones with a unique class of chiral stationary phases (CSPs) based on cyclofructans (CFs). Separations were achieved for all but 2 analytes, with 17 compounds attaining baseline separation having resolution values up to 4.0. Most separations obtained in HPLC could be transferred to SFC, but the HPLC resolutions were generally better due to greater enantiomeric selectivity values. A structure-separation relationship (SSR) was developed to identify important structural features for separation of this class of compounds using CF-based CSPs. Preliminary studies are also presented that demonstrate the utility of the CF CSPs to investigate the base-induced enantiomerization of α-aryl ketones. It was demonstrated that even small amounts of base (0.01%. v/v) in the mobile phase results in rapid, on-column, enantiomerization. Lastly, CSPs composed of superficially porous particles were used to achieve comparable separations of this class of chiral compounds, but at a fraction of the analysis time compared to CSPs composed of fully porous particles.

Original languageEnglish (US)
Pages (from-to)45-54
Number of pages10
JournalJournal of Chromatography A
Volume1427
DOIs
StatePublished - Jan 4 2016

Keywords

  • Cyclofructan chiral stationary phase
  • Enantiomerization
  • HPLC and SFC enantiomeric separation
  • Structure-separation relationship (SSR)
  • Superficially porous particle
  • α-Aryl ketone

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Biochemistry

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