Synthesis of L-arabinose-based crown ethers and their application as enantioselective phase transfer catalysts

Tamás Szabó, Zsolt Rapi, G. Keglevich, A. Szöllösy, L. Drahos, P. Bakó

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

New chiral monoaza-15-crown-5 type macrocycles anellated to 3,4-O-isopropylidene-β-L-arabinopyranose (5a-b), to β-L- arabinopyranose (6) and to 3,4-O-benzyliden-β-L-arabinopyranose (11) have been synthesized. The cation binding ability of the new lariat ethers was evaluated by the picrate extraction method in liquid-liquid system. Some representatives of these crown ethers showed moderate asymmetric induction as chiral phase transfer catalysts, among them 11 with a benzylidene group proved to be the most efficient one inducing 64% ee in the Michael addition of 2-nitropropane to chalcone and 61% ee in the addition of diethyl acetamidomalonate to trans-β-nitrostyrene. An induction of 65% ee was observed in the epoxidation of a chalcone analogue with tert-butyl hydroperoxide in the presence of catalyst 5a.

Original languageEnglish
Pages (from-to)36-48
Number of pages13
JournalArkivoc
Volume2012
Issue number8
Publication statusPublished - Jun 17 2012

Fingerprint

Crown Ethers
Chalcone
Arabinose
tert-Butylhydroperoxide
Catalysts
Ethers
Epoxidation
Liquids
Cations
2-nitropropane
15-crown-5
picric acid
propylene

Keywords

  • Asymmetric catalysis
  • Chiral crown ether
  • Michael addition
  • Phase transfer catalysis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of L-arabinose-based crown ethers and their application as enantioselective phase transfer catalysts. / Szabó, Tamás; Rapi, Zsolt; Keglevich, G.; Szöllösy, A.; Drahos, L.; Bakó, P.

In: Arkivoc, Vol. 2012, No. 8, 17.06.2012, p. 36-48.

Research output: Contribution to journalArticle

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AU - Szabó, Tamás

AU - Rapi, Zsolt

AU - Keglevich, G.

AU - Szöllösy, A.

AU - Drahos, L.

AU - Bakó, P.

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