Asymmetric phase transfer Darzens reactions catalyzed by d-glucose- and d-mannose-based chiral crown ethers

Zsolt Rapi, P. Bakó, G. Keglevich, Áron Szöllsy, L. Drahos, Adrienn Botyánszki, Tamás Holczbauer

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Liquid-liquid phase asymmetric Darzens condensations were carried out in the presence of d-glucose- and d-mannose-based crown ethers 1 and 2 as the catalyst. The use of d-glucose-based lariat ether 1 as the catalyst gave the best results. The reaction of 4-phenyl-α-chloroacetophenone, 2-chloro-1-tetralone, and 2-chloro-1-indanone with various aromatic aldehydes afforded the corresponding aromatic α,β-epoxyketones in moderate to high enantiomeric excess (ee up to 96%) under mild reaction conditions. The substituents of the benzaldehyde used as the reactants had a significant impact on the chemical yields and enantiomeric excess. The absolute configuration of some epoxyketone products was determined by single-crystal X-ray analysis.

Original languageEnglish
Pages (from-to)489-496
Number of pages8
JournalTetrahedron Asymmetry
Volume23
Issue number6-7
DOIs
Publication statusPublished - Apr 15 2012

Fingerprint

Crown Ethers
Crown ethers
Mannose
glucose
Glucose
ethers
omega-Chloroacetophenone
Tetralones
catalysts
Catalysts
X ray analysis
Liquids
Aldehydes
aldehydes
Ether
Condensation
Ethers
liquid phases
condensation
Single crystals

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Asymmetric phase transfer Darzens reactions catalyzed by d-glucose- and d-mannose-based chiral crown ethers. / Rapi, Zsolt; Bakó, P.; Keglevich, G.; Szöllsy, Áron; Drahos, L.; Botyánszki, Adrienn; Holczbauer, Tamás.

In: Tetrahedron Asymmetry, Vol. 23, No. 6-7, 15.04.2012, p. 489-496.

Research output: Contribution to journalArticle

Rapi, Zsolt ; Bakó, P. ; Keglevich, G. ; Szöllsy, Áron ; Drahos, L. ; Botyánszki, Adrienn ; Holczbauer, Tamás. / Asymmetric phase transfer Darzens reactions catalyzed by d-glucose- and d-mannose-based chiral crown ethers. In: Tetrahedron Asymmetry. 2012 ; Vol. 23, No. 6-7. pp. 489-496.
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