Enantioseparation of secondary alcohols by diastereoisomeric salt formation

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9 Citations (Scopus)

Abstract

A general method was found for the resolution of the racemic 1-phenyl-1-propanol (1) and 1-phenyl-2-propanol (2) with various resolving agents. Monoesters of the alcohols were prepared, which were then reacted with different chiral bases. Successful optical resolutions were achieved only with the maleic acid monoesters (3 and 6). Alcohol 1 has been resolved to >99% enantiomeric excess by diastereoisomeric salt formation via its maleic acid monoester (3) using cinchonidine (9) as resolving agent. Alcohol 2 has been obtained in 98% enantiomeric excess by diastereoisomeric salt formation via its the maleic acid monoester (6) using (+)-dehydroabietylamine (11) as resolving agent.

Original languageEnglish
Pages (from-to)116-120
Number of pages5
JournalChirality
Volume18
Issue number2
DOIs
Publication statusPublished - Feb 8 2006

Keywords

  • Diastereoisomeric salt
  • Enantiomer
  • Monoester
  • Optical resolution
  • Resolving agent

ASJC Scopus subject areas

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

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