Asymmetric C-C bond forming reactions with chiral crown catalysts derived from D-glucose and D-galactose

P. Bakó, Erzsébet Czinege, Tibor Bakó, M. Czugler, L. Tőke

Research output: Contribution to journalArticle

91 Citations (Scopus)

Abstract

New chiral monoaza-15-crown-5 derivatives anellated to methyl-4,6-O- benzylidene-α-D-glucopyranoside 2a, 2e, 2g-i and to methyl-4,6-O- benzylidene-α-D-galactopyranoside 3a, 3e, 3i have been synthesized. These crown ethers showed significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (87% ee), in the Darzens condensation of phenacyl chloride with benzaldehyde (71% ee) and in the self-condensation of phenacyl chloride (64% ee) to give 14. The absolute configurations of (-)-(2R,3S)-epoxy-3-(4-chlorophenyl)-1-phenyl-1- propanone 12 and (-)-4-chloro-(2R,3S)-epoxy-1,3-diphenyl-1-butanone 14 have also been determined by X-ray diffraction. (C) 1999 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4539-4551
Number of pages13
JournalTetrahedron Asymmetry
Volume10
Issue number23
Publication statusPublished - Dec 3 1999

Fingerprint

galactose
Crowns
Galactose
glucose
Glucose
Chlorides
Condensation
nitropropane
condensation
chlorides
Butanones
Crown Ethers
Chalcone
catalysts
Crown ethers
Catalysts
X-Ray Diffraction
ethers
induction
Derivatives

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Asymmetric C-C bond forming reactions with chiral crown catalysts derived from D-glucose and D-galactose. / Bakó, P.; Czinege, Erzsébet; Bakó, Tibor; Czugler, M.; Tőke, L.

In: Tetrahedron Asymmetry, Vol. 10, No. 23, 03.12.1999, p. 4539-4551.

Research output: Contribution to journalArticle

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