Synthesis of alkyl α- and β-d-glucopyranoside-based chiral crown ethers and their application as enantioselective phase-transfer catalysts

Ádám Pálvölgyi, Zsolt Rapi, Olivér Ozohanics, Gábor Tóth, György Keglevich, Péter Bakó

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Abstract

Chiral monoaza-15-crown-5-type lariat ethers annelated to alkyl 4,6-O-benzylidene-α- and β-d-glucopyranosides have been synthesized. These macrocycles generated significant asymmetric induction as phase-transfer catalysts in a few two-phase reactions. The catalytic effect of the lariat ethers with methoxy, ethoxy, and i-propoxy substituents on C-1 of the sugar unit in both α and β positions was compared. In liquid–liquid two-phase reactions, the nature and position of the substituents did not have much effect. The α-anomers were somewhat more efficient in terms of enantioselectivity than the β forms. In asymmetric Darzens condensations, in the epoxidation of trans-chalcone, in the Michael addition of β-nitrostyrene and diethyl acetamidomalonate, and in the reaction of 2-benzylidene-1,3-indandione with diethyl bromomalonate, maximum enantioselectivities of 73, 94, 78, and 72%, respectively, were obtained in presence of glucopyranoside-based lariat ethers as catalysts.

Original languageEnglish
Pages (from-to)1627-1645
Number of pages19
JournalResearch on Chemical Intermediates
Volume44
Issue number3
DOIs
Publication statusPublished - Mar 1 2018

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Keywords

  • Asymmetric reaction
  • Chiral crown ether
  • Phase-transfer catalysis

ASJC Scopus subject areas

  • Chemistry(all)

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