Catalytic investigation of (1R,2S)-(-)-N-dodecyl-N-methylephedrinium bromide immobilized on montmorillonite in the enantioselective alkylation of benzaldehyde with diethylzinc

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Abstract

The optically active cationic surfactant (1R,2S)-(-)-N-dodecyl-N-methylephedrinium bromide (DMEB) was immobilized on montmorillonite (M) via cation exchange. XRD studies revealed that the resulting hydrophobic clay organocomplex dodecylmethylephedrinium-montmorillonite (DME-M) underwent a pronounced swelling in ethanol, tetrahydrofuran and toluene. The catalytic behaviour of the heterogenized surfactant was investigated for the enantioselective addition of diethylzinc to benzaldehyde and the results were compared with those obtained for DMEB in a homogeneous reaction, under otherwise the same conditions. The utilization of both DMEB and DME-M afforded pronounced selectivities for the formation of 1-phenyl-1-propanol. The application of DME-M was found to result in higher conversions and lower enantioselectivities than those observed for DMEB. The effect of the reaction temperature on the catalytic behaviour of the pristine and immobilized chiral surfactant was also examined.

Original languageEnglish
Pages (from-to)1404-1409
Number of pages6
JournalCatalysis Communications
Volume9
Issue number6
DOIs
Publication statusPublished - Mar 31 2008

Fingerprint

Bentonite
Alkylation
Clay minerals
Bromides
Surface-Active Agents
Surface active agents
Enantioselectivity
Cationic surfactants
Toluene
Propanol
Swelling
Cations
Ion exchange
Clay
Ethanol
Positive ions
(1R,2S)-(-)-N-dodecyl-N-methylephedrinium bromide
diethylzinc
benzaldehyde
Temperature

Keywords

  • Cationic surfactant
  • Diethylzinc
  • Enantiomeric excess
  • Enantioselective alkylation
  • Ephedrine
  • Montmorillonite
  • Swelling

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

Cite this

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title = "Catalytic investigation of (1R,2S)-(-)-N-dodecyl-N-methylephedrinium bromide immobilized on montmorillonite in the enantioselective alkylation of benzaldehyde with diethylzinc",
abstract = "The optically active cationic surfactant (1R,2S)-(-)-N-dodecyl-N-methylephedrinium bromide (DMEB) was immobilized on montmorillonite (M) via cation exchange. XRD studies revealed that the resulting hydrophobic clay organocomplex dodecylmethylephedrinium-montmorillonite (DME-M) underwent a pronounced swelling in ethanol, tetrahydrofuran and toluene. The catalytic behaviour of the heterogenized surfactant was investigated for the enantioselective addition of diethylzinc to benzaldehyde and the results were compared with those obtained for DMEB in a homogeneous reaction, under otherwise the same conditions. The utilization of both DMEB and DME-M afforded pronounced selectivities for the formation of 1-phenyl-1-propanol. The application of DME-M was found to result in higher conversions and lower enantioselectivities than those observed for DMEB. The effect of the reaction temperature on the catalytic behaviour of the pristine and immobilized chiral surfactant was also examined.",
keywords = "Cationic surfactant, Diethylzinc, Enantiomeric excess, Enantioselective alkylation, Ephedrine, Montmorillonite, Swelling",
author = "A. Mastalir and Z. Kir{\'a}ly",
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AU - Király, Z.

PY - 2008/3/31

Y1 - 2008/3/31

N2 - The optically active cationic surfactant (1R,2S)-(-)-N-dodecyl-N-methylephedrinium bromide (DMEB) was immobilized on montmorillonite (M) via cation exchange. XRD studies revealed that the resulting hydrophobic clay organocomplex dodecylmethylephedrinium-montmorillonite (DME-M) underwent a pronounced swelling in ethanol, tetrahydrofuran and toluene. The catalytic behaviour of the heterogenized surfactant was investigated for the enantioselective addition of diethylzinc to benzaldehyde and the results were compared with those obtained for DMEB in a homogeneous reaction, under otherwise the same conditions. The utilization of both DMEB and DME-M afforded pronounced selectivities for the formation of 1-phenyl-1-propanol. The application of DME-M was found to result in higher conversions and lower enantioselectivities than those observed for DMEB. The effect of the reaction temperature on the catalytic behaviour of the pristine and immobilized chiral surfactant was also examined.

AB - The optically active cationic surfactant (1R,2S)-(-)-N-dodecyl-N-methylephedrinium bromide (DMEB) was immobilized on montmorillonite (M) via cation exchange. XRD studies revealed that the resulting hydrophobic clay organocomplex dodecylmethylephedrinium-montmorillonite (DME-M) underwent a pronounced swelling in ethanol, tetrahydrofuran and toluene. The catalytic behaviour of the heterogenized surfactant was investigated for the enantioselective addition of diethylzinc to benzaldehyde and the results were compared with those obtained for DMEB in a homogeneous reaction, under otherwise the same conditions. The utilization of both DMEB and DME-M afforded pronounced selectivities for the formation of 1-phenyl-1-propanol. The application of DME-M was found to result in higher conversions and lower enantioselectivities than those observed for DMEB. The effect of the reaction temperature on the catalytic behaviour of the pristine and immobilized chiral surfactant was also examined.

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KW - Montmorillonite

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