Development of L-proline-based Chiral Ionic Liquids for asymmetric Michael Reaction

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Abstract

Different Chiral Ionic Liquids (CIL) based on L-proline have been developed. Simple and efficient synthetic methodologies are used, allowing preparation in good yields for twelve novel CILs using L-proline as a cation or anion combined with suitable counter-ions. A detailed physical and chemical characterization of the CILs was performed to evaluate the influence of counter-ions on the final properties. The most promissory CILs were tested as efficient chiral catalysts in IL media for asymmetric Michael addition reactions of ketones and aldehydes to nitro-olefins. Similar or even better conversions and enantioselectivities (ee up to 95%) compared to the original L-proline were achieved. Additionally, a good product extraction performance using supercritical CO2 processes was obtained.

Original languageEnglish
Article number270
Number of pages16
JournalCatalysts
Volume13
DOIs
Publication statusPublished - 25 Jan 2023

Keywords

  • asymmetric Michael reaction
  • chiral ionic liquids
  • L-proline
  • supercritical CO extraction

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