Synthesis of D-mannose-based azacrown ethers and their application in enantioselective reactions

Péter Bakó, Attila Makó, György Keglevich, Miklós Kubinyi, Krisztina Pál

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New chiral monoaza-15-crown-5 compounds anellated to methyl-4,6-O- benzylidene-α-D-mannopyranosides 2a-f have been synthesized. These crown ethers showed significant asymmetric induction as phase-transfer catalysts in the Michael addition of 2-nitropropane to chalcone (92% ee), in the Darzens condensation of phenacyl chloride with benzaldehyde (45% ee) and in the epoxidation of chalcones with tert-butyl-hydroperoxide (82% ee). The enantioselectivity was effected by the substituents at the nitrogen atom of the crown ring. The absolute configurations of epoxyketones 10 were determined by CD spectroscopy.

Original languageEnglish
Pages (from-to)1861-1871
Number of pages11
JournalTetrahedron Asymmetry
Issue number10
Publication statusPublished - May 23 2005


ASJC Scopus subject areas

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

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