Synthesis of D-glucose-based Azacrown Ethers with phosphinoxidoalkyl side chains and their application to an enantioselective reaction

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Abstract

Five chiral α-D-glucose-based monoaza-15-crown-5 ethers with phosphinoxidoalkyl side chains of one to five carbon atoms (5a-e) have been synthesised. The cation binding ability of the new lariat ethers was evaluated by the picrate extraction method. The substituents at the nitrogen atom were not a major influence on the cation extraction ability of the azacrown ether; the compounds showed, however, a significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (95% ee).

Original languageEnglish
Pages (from-to)207-212
Number of pages6
JournalJournal of Inclusion Phenomena
Volume40
Issue number3
DOIs
Publication statusPublished - Jul 1 2001

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Keywords

  • Azacrown ethers
  • Chiral lariat ethers
  • Enantioselective synthesis
  • Extraction ability
  • Monoaza-15-crown-5
  • Phosphinoxidoalkyl side chain

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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