Enantiomerically pure chiral phenazino-crown ethers: Synthesis, preliminary circular dichroism spectroscopic studies and complexes with the enantiomers of 1-arethyl ammonium salts

Erika Samu, Péter Huszthy, László Somogyi, Miklós Hollósi

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35 Citations (Scopus)

Abstract

Enantiomerically pure chiral crown ethers containing the phenazine unit [(R,R)-2-(S,S)-8] were prepared by two types of cyclization reactions. Ligands (R,R)-2, (R,R)-3, (S,S)-4, (R,R)-5, (R,R)-6 and (R,R)-7 were prepared from phenazine-1,9-diol 9 and the appropriate ditosylates (S,S)-10-(S,S)-15 in weak basic conditions with complete inversion of configuration. Ligands (S,S)-2, (S,S)-7 and (S,S)-8, however, were prepared from 1,9-dichlorophenazine 19 and the appropriate diols (S,S)-16-(S,S)-18 in strong basic conditions with retention of configuration. Enantiomeric recognition of most of the chiral ligands with α-(1-naphthyl)ethylammonium perchlorate (NEA) and α-phenylethylammonium perchlorate (PEA) has been studied by CD spectroscopy.

Original languageEnglish
Pages (from-to)2775-2795
Number of pages21
JournalTetrahedron Asymmetry
Volume10
Issue number14
DOIs
Publication statusPublished - Jul 16 1999

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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