High-performance liquid chromatographic enantioseparation of methanobenzazocines

William M. Barker, Karin Worm, Roland E. Dolle

Research output: Contribution to journalArticlepeer-review

4 Scopus citations


Chiral recognition and resolution of methanobenzazocines was investigated by HPLC using polysaccharide, Pirkle-type, native and derivatized β-cyclodextrin chiral stationary phases. Enantioseparation of phenyl substituted 2,6-methanobenzazocines was achieved with multiple chiral stationary phases throughout the classes described. Chiral resolution of the enantiomers of 1,5-methano-3-methyl-6-oxo-1,2,3,4,5,6-hexahydro-3-benzazocine was produced on both polysaccharide and Pirkle-type phases. In the case of 1,5-methano-3-methyl-6-phenyl-1,2,3,4,5,6-hexahydro-3-benzazocine only a dinitrophenyl substituted β-cyclodextrin produced a separation of enantiomers.

Original languageEnglish
Pages (from-to)7708-7714
Number of pages7
JournalJournal of Chromatography A
Issue number45
StatePublished - Nov 6 2009


  • Benzazocine
  • Benzomorphans
  • Chiral separation
  • Cyclodextrin
  • Enantioselective
  • HPLC
  • Polysaccharide and Pirkle-type chiral stationary phases
  • Racemic


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