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.
- Switchable catalysis
- Trifunctional organocatalysis
- Moritae-Baylise-Hillman reaction