Computational design for enantioselective CO2 capture: asymmetric frustrated Lewis pairs in epoxide transformations

Maxime Ferrer*, Iñigo Iribarren, Tim Renningholtz, Ibon Alkorta, Cristina Trujillo*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Carbon capture and utilisation (CCU) technologies offer a compelling strategy to mitigate rising atmospheric carbon dioxide levels. Despite extensive research on the CO2 insertion into epoxides to form cyclic carbonates, the stereochemical implications of this reaction have been largely overlooked, despite the prevalence of racemic epoxide solutions. This study introduces an in silico approach to design asymmetric frustrated Lewis pairs (FLPs) aimed at controlling reaction stereochemistry. Four FLP scaffolds, incorporating diverse Lewis acids (LA), Lewis bases (LB), and substituents, were assessed via volcano plot analysis to identify the most promising catalysts. By strategically modifying LB substituents to induce asymmetry, a stereoselective catalytic scaffold was developed, favouring one enantiomer from both epoxide enantiomers. This work advances the in silico design of FLPs, highlighting their potential as asymmetric CCU catalysts with implications for optimising catalyst efficiency and selectivity in sustainable chemistry applications.

Original languageEnglish
Pages (from-to)2668-2681
Number of pages14
JournalBeilstein Journal of Organic Chemistry
Volume20
DOIs
Publication statusPublished - 2024

Keywords

  • asymmetric catalysis
  • carbon dioxide
  • CO
  • epoxide
  • frustrated Lewis pairs (FLPs)
  • volcano plot

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