Chiral separation on various modified amino alcohol-derived HPLC chiral stationary phases

Chirality. 2016 Apr;28(4):276-81. doi: 10.1002/chir.22576. Epub 2016 Feb 12.


3,5-Dinitrobenzoyl chloride was previously used for the preparation of (R)-phenylglycinol- and (S)-leucinol-derived chiral stationary phases. In this study, 3,5-bis(trifluoromethyl)benzoyl chloride, 2-furoyl chloride, 2-theonyl chloride, 10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride, diphenylcarbamoyl chloride, and 1-adamantanecarbonyl chloride were used to prepare six new phenylglycinol-derived chiral stationary phases (CSPs) and five new leucinol-derived CSPs. Using these 11 CSPs, chiral separation of nine π-acidic amino acid derivatives and five π-basic compounds was performed, and the separation results were compared. An adamantyl-derived CSP showed good separation.

Keywords: (R)-phenylglycinol; (S)-leucinol; adamantyl-derived CSP; chiral stationary phase; different acid chlorides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adamantane / analogs & derivatives
  • Adamantane / chemistry*
  • Amino Alcohols / chemistry*
  • Biphenyl Compounds / chemistry
  • Chromatography, High Pressure Liquid
  • Cycloheptanes / chemistry
  • Ethanolamines / chemistry
  • Stereoisomerism


  • 1-adamantanecarbonyl chloride
  • 10,11-dihydro-5H-dibenzo(a,d)cycloheptene
  • Amino Alcohols
  • Biphenyl Compounds
  • Cycloheptanes
  • Ethanolamines
  • N-phenylethanolamine
  • diphenylcarbamoyl chloride
  • Adamantane