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

Paper ID Volume ID Publish Year Pages File Format Full-Text
52164 46865 2008 6 PDF Available
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
Ephedrine; Cationic surfactant; Montmorillonite; Diethylzinc; Enantioselective alkylation; Swelling; Enantiomeric excess
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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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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 9, Issue 6, 31 March 2008, Pages 1404–1409
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us