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Cationic chiral surfactant based micelle-guided asymmetric Morita-Baylis-Hillman reaction

Paper ID Volume ID Publish Year Pages File Format Full-Text
49693 46760 2016 4 PDF Available
Title
Cationic chiral surfactant based micelle-guided asymmetric Morita-Baylis-Hillman reaction
Abstract

•A cationic chiral surfactant was utilized in inducing asymmetry to MBH-reaction.•Proton NMR studies were carried out to determine the locus of the reaction.•The protocol is non-hazardous that favors faster reaction rates and high yields.

Cationic chiral surfactant (1R, 2S)-(−)-N-dodecyl-N-methylephedrinium bromide (DMEB) was utilized for the first time in inducing asymmetry to Morita-Baylis-Hillman reaction in aqueous medium. Proton NMR studies carried out to determine the locus of the reaction in micro-heterogeneous micellar environment, were found useful in proposing a plausible model for asymmetric induction. This work demonstrates that under such mild and non-hazardous reactions conditions, the reaction rates increase, good yields are favored and above all reasonable enantiomeric excesses are obtained.

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Keywords
Ephedrinium salts; Morita-Baylis-Hillman reaction; Asymmetric induction; Enantiomeric excess; Micellar micro-environment
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Cationic chiral surfactant based micelle-guided asymmetric Morita-Baylis-Hillman reaction
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 83, 5 August 2016, Pages 58–61
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
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Full-text PDF Download
Online Support
Any Questions? feel free to contact us