Asymmetric phase transfer Darzens reactions catalyzed by d-glucose- and d-mannose-based chiral crown ethers

Zsolt Rapi, Péter Bakó, György Keglevich, Áron Szöllsy, László Drahos, Adrienn Botyánszki, Tamás Holczbauer

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Abstract

Liquid-liquid phase asymmetric Darzens condensations were carried out in the presence of d-glucose- and d-mannose-based crown ethers 1 and 2 as the catalyst. The use of d-glucose-based lariat ether 1 as the catalyst gave the best results. The reaction of 4-phenyl-α-chloroacetophenone, 2-chloro-1-tetralone, and 2-chloro-1-indanone with various aromatic aldehydes afforded the corresponding aromatic α,β-epoxyketones in moderate to high enantiomeric excess (ee up to 96%) under mild reaction conditions. The substituents of the benzaldehyde used as the reactants had a significant impact on the chemical yields and enantiomeric excess. The absolute configuration of some epoxyketone products was determined by single-crystal X-ray analysis.

Original languageEnglish
Pages (from-to)489-496
Number of pages8
JournalTetrahedron Asymmetry
Volume23
Issue number6-7
DOIs
Publication statusPublished - Apr 15 2012

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ASJC Scopus subject areas

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

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