Synthesis of new enantiopure dimethyl-substituted pyridino-18-crown-6 ethers containing a hydroxymethyl, a formyl, ora carboxyl group at position 4 of the pyridine ring for enantiomeric recognition studies

József Kupai, Péter Huszthy, Marianna Katz, Tünde Tóth

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2 Citations (Scopus)

Abstract

An enantiomerically pure dimethyl-substituted pyridino-18-crown-6 ether containing a hydroxymethyl group at position 4 of the pyridine ring [(S,S )-1] has been prepared. This by Swern oxidation gave the formyl-substituted [( S,S)-2], then by further oxidation carboxy-substituted [(S,S)-3 ] pyridino-18-crown-6 ether derivatives. These enantiopure dimethyl-substituted pyridino-18-crown-6 ethers [( S,S )-1-(S,S )-3 ] are good candidates for enantiomeric recognition studies and also very useful precursors for enantioselective sensor and selector molecules with wide applications.

Original languageEnglish
Pages (from-to)134-145
Number of pages12
JournalArkivoc
Volume2012
Issue number5
DOIs
Publication statusPublished - Mar 11 2012

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Keywords

  • Chiral crown ethers
  • Chiral stationary phases
  • Enantiomeric recognition
  • Fenton-type reaction
  • Macrocycles
  • Pyridino-18-crown-6 ligands

ASJC Scopus subject areas

  • Organic Chemistry

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