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

P. Bakó, Attila Makó, G. Keglevich, M. Kubinyi, Krisztina Pál

Research output: Contribution to journalArticle

60 Citations (Scopus)

Abstract

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
Volume16
Issue number10
DOIs
Publication statusPublished - May 23 2005

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Crown Compounds
nitropropane
Chalcones
Crown Ethers
Chalcone
tert-Butylhydroperoxide
Crown ethers
epoxidation
Ethers
Epoxidation
Enantioselectivity
Mannose
Crowns
nitrogen atoms
Chlorides
Condensation
ethers
Spectrum Analysis
induction
Nitrogen

ASJC Scopus subject areas

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

Cite this

Synthesis of D-mannose-based azacrown ethers and their application in enantioselective reactions. / Bakó, P.; Makó, Attila; Keglevich, G.; Kubinyi, M.; Pál, Krisztina.

In: Tetrahedron Asymmetry, Vol. 16, No. 10, 23.05.2005, p. 1861-1871.

Research output: Contribution to journalArticle

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