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

• 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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