Chiral separation machinery using new crystalline inclusion hosts: Match/mismatch in the enantiomer recognition of (R,S)-1-methoxy-2-propanol effected by a borneol/fenchol building block exchange in the host molecule

Mátyás Czugler, Petros P. Korkas, Petra Bombicz, Wilhelm Seichter, Edwin Weber

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

New chiral host molecules 1 and 2 involving a bulky terpenoid unit and aromatic ethyne spacer groups were synthesized using Pd-catalyzed cross- coupling reactions of (+)-2α-ethynyl-2β-hydroxybornane (4) or (+)-2α- ethynyl-2β-hydroxyfenchane (5) with 9,10-dibromoanthracene. Host compounds 1 and 2 form crystalline inclusions with 1-methoxy-2-propanol (3) in 1:1 and 1:2 stoichiometry, respectively. In the case of 1, complete enantiomer resolution (ee > 99%) of 3 is effected in one cocrystallization step. However, constitutional isomer 2 failed in the enantiomer separation of 3, which might be explained due to the different crystal lattice buildup of these cocrystals.

Original languageEnglish
Pages (from-to)203-210
Number of pages8
JournalChirality
Volume9
Issue number3
DOIs
Publication statusPublished - Jan 1 1997

Keywords

  • Chiral selectors
  • bulky diols
  • chiroselective cocrystallization
  • clathrate hosts
  • crystal packing analysis
  • host-guest complexes
  • inclusion compounds
  • natural product derived hosts
  • optically active hosts

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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