Switchable pyrrole-based hydrogen bonding motif in enantioselective trifunctional organocatalysis

Sviatoslav S. Eliseenko, Fei Liu*

*Corresponding author for this work

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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
JournalTetrahedron
Volume75
Issue number4
DOIs
Publication statusPublished - 25 Jan 2019

Keywords

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

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