Synthesis, extraction ability and application in asymmetric synthesis of azacrown ethers derived from D-glucose

Péter Bakó, Kristóf Vízvárdi, Suzanne Toppet, Erik Van Der Eycken, Georges J. Hoornaert, László Tõke

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

A number of new chiral monoaza-15-crown-5 derivatives (4-9) and lariat ethers (10-15) anellated to phenyl-β-D-glucopyranoside have been synthesized. Their extracting ability was measured with alkali metal (Li, Na, K) and ammonium cations. The derivatives show significant asymmetric induction as phase transfer catalysts in the Michael addition of 2- nitropropane to chalcone (82% ee) although in low yield, and in the Darzens condensation of phenacyl chloride with benzaldehyde (74% ee). The substituent at the nitrogen atom of the crown ethers has a major influence on both the extraction ability and the enantioselectivity.

Original languageEnglish
Pages (from-to)14975-14988
Number of pages14
JournalTetrahedron
Volume54
Issue number49
DOIs
Publication statusPublished - Dec 3 1998

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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