Synthesis of new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety

Ilona Kovács, Péter Huszthy, Ferenc Bertha, Dénes Sziebert

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Seven new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety were prepared starting from optically active dialkyl-substituted oligoethylene glycols and phosphorus oxychloride followed by mild hydrolysis of the resulting macrocyclic chlorophosphates. Pentaethylene glycols having primary hydroxyl groups gave good yields of 17-crown-6 type ethers. Pentaethylene glycols with secondary hydroxyl groups rendered about the same amount of 17-crown-6 ethers and open chain dihydrogenphosphates in low yields. Tetraethylene glycols are reluctant to undergo macrocyclization with phosphorus oxychloride, especially the ones which contain secondary hydroxyl groups.

Original languageEnglish
Pages (from-to)2538-2547
Number of pages10
JournalTetrahedron Asymmetry
Volume17
Issue number17
DOIs
Publication statusPublished - Oct 2 2006

ASJC Scopus subject areas

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

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