Synthesis of D-glucose-based Azacrown Ethers with phosphinoxidoalkyl side chains and their application to an enantioselective reaction

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Abstract

Five chiral α-D-glucose-based monoaza-15-crown-5 ethers with phosphinoxidoalkyl side chains of one to five carbon atoms (5a-e) have been synthesised. The cation binding ability of the new lariat ethers was evaluated by the picrate extraction method. The substituents at the nitrogen atom were not a major influence on the cation extraction ability of the azacrown ether; the compounds showed, however, a significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (95% ee).

Original languageEnglish
Pages (from-to)207-212
Number of pages6
JournalJournal of Inclusion Phenomena
Volume40
Issue number3
DOIs
Publication statusPublished - Jul 2001

Fingerprint

Ethers
glucose
Cations
ethers
Crown Ethers
Chalcone
Glucose
Atoms
synthesis
cations
nitropropane
Ether
picrates
chalcone
Nitrogen
Carbon
binding capacity
catalysts
nitrogen atoms
Catalysts

Keywords

  • Azacrown ethers
  • Chiral lariat ethers
  • Enantioselective synthesis
  • Extraction ability
  • Monoaza-15-crown-5
  • Phosphinoxidoalkyl side chain

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

Cite this

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abstract = "Five chiral α-D-glucose-based monoaza-15-crown-5 ethers with phosphinoxidoalkyl side chains of one to five carbon atoms (5a-e) have been synthesised. The cation binding ability of the new lariat ethers was evaluated by the picrate extraction method. The substituents at the nitrogen atom were not a major influence on the cation extraction ability of the azacrown ether; the compounds showed, however, a significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (95{\%} ee).",
keywords = "Azacrown ethers, Chiral lariat ethers, Enantioselective synthesis, Extraction ability, Monoaza-15-crown-5, Phosphinoxidoalkyl side chain",
author = "Tibor Nov{\'a}k and P. Bak{\'o} and G. Keglevich and A. Dob{\'o} and K. V{\'e}key and L. Tőke",
year = "2001",
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doi = "10.1023/A:1011840831308",
language = "English",
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TY - JOUR

T1 - Synthesis of D-glucose-based Azacrown Ethers with phosphinoxidoalkyl side chains and their application to an enantioselective reaction

AU - Novák, Tibor

AU - Bakó, P.

AU - Keglevich, G.

AU - Dobó, A.

AU - Vékey, K.

AU - Tőke, L.

PY - 2001/7

Y1 - 2001/7

N2 - Five chiral α-D-glucose-based monoaza-15-crown-5 ethers with phosphinoxidoalkyl side chains of one to five carbon atoms (5a-e) have been synthesised. The cation binding ability of the new lariat ethers was evaluated by the picrate extraction method. The substituents at the nitrogen atom were not a major influence on the cation extraction ability of the azacrown ether; the compounds showed, however, a significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (95% ee).

AB - Five chiral α-D-glucose-based monoaza-15-crown-5 ethers with phosphinoxidoalkyl side chains of one to five carbon atoms (5a-e) have been synthesised. The cation binding ability of the new lariat ethers was evaluated by the picrate extraction method. The substituents at the nitrogen atom were not a major influence on the cation extraction ability of the azacrown ether; the compounds showed, however, a significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (95% ee).

KW - Azacrown ethers

KW - Chiral lariat ethers

KW - Enantioselective synthesis

KW - Extraction ability

KW - Monoaza-15-crown-5

KW - Phosphinoxidoalkyl side chain

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