Switchable pyrrole-based hydrogen bonding motif in enantioselective trifunctional organocatalysis

Sviatoslav S. Eliseenko, Fei Liu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)


    Pyrroles are versatile chemical motifs for molecular recognition or ligand design but their utility as catalytic components are underexplored. We incorporated a pyrrole motif into our acid-switchable, MAP-based trifunctional organocatalytic system. The switching-on of this system by an external Brønsted acid, 3-methyl benzoic acid, presented proficient catalysis in both aza-Morita–Baylis–Hillman (MBH, up to >95% conversion and 88% ee over 3 h) and MBH (up to 81% conversion and 77% ee over 6 h) reactions. The enhanced catalytic generality and proficiency may be due to the new cooperativity via CH/π interactions between pyrrole and the acid switch.

    Original languageEnglish
    Pages (from-to)518-526
    Number of pages9
    Issue number4
    Publication statusPublished - 25 Jan 2019


    • Switchable catalysis
    • Cooperativity
    • Trifunctional organocatalysis
    • Enantioselectivity
    • Pyrroles
    • Moritae-Baylise-Hillman reaction


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