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

P. Bakó, Kristóf Vízvárdi, Suzanne Toppet, Erik Van Der Eycken, Georges J. Hoornaert, L. Tőke

Research output: Contribution to journalArticle

55 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
Publication statusPublished - Dec 3 1998

Fingerprint

Alkali Metals
Crown Ethers
Chalcone
Ethers
Ammonium Compounds
Cations
Chlorides
Nitrogen
Derivatives
Glucose
Enantioselectivity
Condensation
Atoms
Catalysts
benzaldehyde
2-nitropropane
15-crown-5

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Bakó, P., Vízvárdi, K., Toppet, S., Van Der Eycken, E., Hoornaert, G. J., & Tőke, L. (1998). Synthesis, extraction ability and application in asymmetric synthesis of azacrown ethers derived from D-glucose. Tetrahedron, 54(49), 14975-14988.

Synthesis, extraction ability and application in asymmetric synthesis of azacrown ethers derived from D-glucose. / Bakó, P.; Vízvárdi, Kristóf; Toppet, Suzanne; Van Der Eycken, Erik; Hoornaert, Georges J.; Tőke, L.

In: Tetrahedron, Vol. 54, No. 49, 03.12.1998, p. 14975-14988.

Research output: Contribution to journalArticle

Bakó, P, Vízvárdi, K, Toppet, S, Van Der Eycken, E, Hoornaert, GJ & Tőke, L 1998, 'Synthesis, extraction ability and application in asymmetric synthesis of azacrown ethers derived from D-glucose', Tetrahedron, vol. 54, no. 49, pp. 14975-14988.
Bakó P, Vízvárdi K, Toppet S, Van Der Eycken E, Hoornaert GJ, Tőke L. Synthesis, extraction ability and application in asymmetric synthesis of azacrown ethers derived from D-glucose. Tetrahedron. 1998 Dec 3;54(49):14975-14988.
Bakó, P. ; Vízvárdi, Kristóf ; Toppet, Suzanne ; Van Der Eycken, Erik ; Hoornaert, Georges J. ; Tőke, L. / Synthesis, extraction ability and application in asymmetric synthesis of azacrown ethers derived from D-glucose. In: Tetrahedron. 1998 ; Vol. 54, No. 49. pp. 14975-14988.
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