Synthesis of L-arabinose-based crown ethers and their application as enantioselective phase transfer catalysts

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New chiral monoaza-15-crown-5 type macrocycles anellated to 3,4-O-isopropylidene-β-L-arabinopyranose (5a-b), to β-L- arabinopyranose (6) and to 3,4-O-benzyliden-β-L-arabinopyranose (11) have been synthesized. The cation binding ability of the new lariat ethers was evaluated by the picrate extraction method in liquid-liquid system. Some representatives of these crown ethers showed moderate asymmetric induction as chiral phase transfer catalysts, among them 11 with a benzylidene group proved to be the most efficient one inducing 64% ee in the Michael addition of 2-nitropropane to chalcone and 61% ee in the addition of diethyl acetamidomalonate to trans-β-nitrostyrene. An induction of 65% ee was observed in the epoxidation of a chalcone analogue with tert-butyl hydroperoxide in the presence of catalyst 5a.

Original languageEnglish
Pages (from-to)36-48
Number of pages13
Issue number8
Publication statusPublished - Jun 17 2012



  • Asymmetric catalysis
  • Chiral crown ether
  • Michael addition
  • Phase transfer catalysis

ASJC Scopus subject areas

  • Organic Chemistry

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