Enantiomeric separation of biaryl atropisomers using cyclofructan based chiral stationary phases

Ross M. Woods, Darshan C. Patel, Yeeun Lim, Zachary S. Breitbach, Hongyin Gao, Craig Keene, Gongqiang Li, László Kürti, Daniel W. Armstrong

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

Normal phase chiral HPLC methods are presented for the enantiomeric separation of 30 biaryl atropisomers including 18 new compounds recently produced via a novel synthetic approach. Three new cyclofructan based chiral stationary phases were evaluated. Separations were achieved for all but six analytes and the LARIHC™ CF6-P alone provided 15 baseline separations. Effects of polar modifiers and temperature effects also were studied. Apparent thermodynamic parameters were determined by van't Hoff plots. Preparative scale methods were developed and employed resulting in the first ever isolation of these novel atropisomers in their pure enantiomeric form. Insights into the mechanism of retention and chiral discrimination are presented.

Original languageEnglish (US)
Pages (from-to)172-181
Number of pages10
JournalJournal of Chromatography A
Volume1357
DOIs
StatePublished - Aug 29 2014

Keywords

  • Atropisomers
  • Biaryls
  • Chiral HPLC
  • Cyclofructans
  • Preparative HPLC

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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    Woods, R. M., Patel, D. C., Lim, Y., Breitbach, Z. S., Gao, H., Keene, C., Li, G., Kürti, L., & Armstrong, D. W. (2014). Enantiomeric separation of biaryl atropisomers using cyclofructan based chiral stationary phases. Journal of Chromatography A, 1357, 172-181. https://doi.org/10.1016/j.chroma.2014.04.080