Enantioseparation of Chiral Alcohols by Complex Formation and Subsequent Supercritical Fluid Extraction

Edit Székely, Béla Simándi, Elemér Fogassy, Sándor Kemény, Ildikó Kmecz

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The very first application of supercritical fluid extraction (SFE) on enantioseparation of alcohols is discussed. Resolutions of three chiral alcohols (trans-2-chloro-cyclohexanol, trans-2-bromo-cyclohexanol, and trans-2-iodo-cyclohexanol) were performed by partial complexation with (-)-O,O′-dibenzoyl-(2R,3R)-tartaric acid monohydrate (DBTA). DBTA formed diastereomeric complexes with all S,S-enantiomers stable enough to extract the unreacted alcohols with supercritical carbon dioxide. Resolution efficiency increased with the size of halogen substituents, and by the proper selection of molar ratio, pure (-)-R,R-trans-2-iodo-cyclohexanol (ee > 99%, yield: 39%) or (+)-S,S-trans-2-iodo-cyclohexanol (ee = 98%, yield: 8%) were prepared in one process step. Achieved resolution efficiency values were much higher in all resolution procedures than in any other known enantioseparation of these racemic compounds. The developed method offers an environmentally friendly, efficient alternative of currently applied resolution processes, also on a preparative scale.

Original languageEnglish
Pages (from-to)783-786
Number of pages4
JournalChirality
Volume15
Issue number9
DOIs
Publication statusPublished - Nov 13 2003

Keywords

  • (-)-O,O′-dibenzoyl-(2R,3R)-tartaric acid monohydrate
  • Carbon dioxide
  • Environmentally friendly chiral resolution
  • Trans-2-bromo-cyclohexanol
  • Trans-2-chlorocyclohexanol
  • trans-2-iodo-cyclohexanol

ASJC Scopus subject areas

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

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