Synthesis of chiral pyridino-15-crown-5 type ligands containing α-D-hexapyranoside unit and their application in asymmetric synthesis

Attila Makó, Péter Bakó, Áron Szöllösy, Tibor Bakó, Csaba Peltz, Péter Keglevich

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9 Citations (Scopus)

Abstract

The synthesis of novel chiral monoaza-15-crown-5 compounds (1-4) with pyridine-ring starting from methyl-4,6-O-benzylidene-α-D-glucopyranoside and methyl-4,6-O-benzylidene-α-D-mannopyranoside by different methods are reported. These crown ethers showed significant asymmetric induction in a Michael addition (up to 80% ee).

Original languageEnglish
Pages (from-to)165-179
Number of pages15
JournalArkivoc
Volume2009
Issue number7
DOIs
Publication statusPublished - Apr 8 2009

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Keywords

  • Asymmetric catalysis
  • Crown compounds
  • Michael addition
  • Phase-transfer catalysis
  • Ring closure

ASJC Scopus subject areas

  • Organic Chemistry

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