Asymmetric C-C bond formation via Darzens condensation and Michael addition using monosaccharide-based chiral crown ethers

P. Bakó, Zsolt Rapi, G. Keglevich, Tamás Szabó, Péter L. Sóti, Tamás Vígh, Alajos Grn, Tamás Holczbauer

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Liquid-liquid phase asymmetric Darzens condensations were promoted by d-glucose- and d-mannose-based crown ethers. The corresponding aromatic and heteroaromatic α,β-epoxyketones were obtained with moderate to high enantioselectivities (up to 96%) as well as diastereoselectivities (up to 98:2) under mild reaction conditions. The absolute configurations of several of the epoxyketones were determined by single crystal X-ray analysis. The Michael additions of diethyl acetylaminomalonate to trans-β-nitroalkenes were carried out in a solid-liquid two-phase system in the presence of a d-glucose-based crown catalyst with up to 99% ee.

Original languageEnglish
Pages (from-to)1473-1476
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number13
DOIs
Publication statusPublished - Mar 30 2011

Fingerprint

Crown Ethers
Monosaccharides
Condensation
Glucose
Liquids
Mannose
Crowns
Enantioselectivity
X ray analysis
X-Rays
Single crystals
Catalysts

Keywords

  • Chiral phase-transfer catalysis
  • Crown compounds
  • Darzens condensation
  • Enantioselectivity
  • Michael addition

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Asymmetric C-C bond formation via Darzens condensation and Michael addition using monosaccharide-based chiral crown ethers. / Bakó, P.; Rapi, Zsolt; Keglevich, G.; Szabó, Tamás; Sóti, Péter L.; Vígh, Tamás; Grn, Alajos; Holczbauer, Tamás.

In: Tetrahedron Letters, Vol. 52, No. 13, 30.03.2011, p. 1473-1476.

Research output: Contribution to journalArticle

Bakó, P. ; Rapi, Zsolt ; Keglevich, G. ; Szabó, Tamás ; Sóti, Péter L. ; Vígh, Tamás ; Grn, Alajos ; Holczbauer, Tamás. / Asymmetric C-C bond formation via Darzens condensation and Michael addition using monosaccharide-based chiral crown ethers. In: Tetrahedron Letters. 2011 ; Vol. 52, No. 13. pp. 1473-1476.
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AU - Sóti, Péter L.

AU - Vígh, Tamás

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