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Asymmetric Michael Addition Mediated by Chiral Ionic Liquids
1Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, 102-8554Tokyo, Japan.
Mini-Reviews in Organic Chemistry
|June 5, 2018
Summary
Chiral ionic liquids are effective catalysts for asymmetric Michael additions. Proline-derived ionic liquids, particularly those enabling enamine/iminium formation, show high chiral induction and recyclability.
Area of Science:
- Organic Chemistry
- Green Chemistry
- Catalysis
Background:
- Chiral ionic liquids (CILs) are increasingly explored for sustainable synthesis.
- Asymmetric Michael additions are crucial carbon-carbon bond-forming reactions.
- Developing efficient and recyclable chiral catalysts is a key challenge.
Purpose of the Study:
- To review chiral ionic liquids for asymmetric Michael additions.
- To classify CILs based on induction mode, role, and structure.
- To highlight proline-derived CILs and their catalytic mechanisms.
Main Methods:
- Literature review of CIL applications in asymmetric Michael additions.
- Classification of CILs by asymmetric induction mechanisms (external/internal).
- Analysis of CIL roles (solvent/catalyst) and structural types (imidazolium, onium, proline derivatives).
Main Results:
- Proline-derived CILs are highly effective catalysts for Michael additions.
- Enamine/iminium formation is a key mechanism for high chiral induction.
- CILs can act as both solvents and catalysts, offering versatility.
- Recyclability of ionic liquid-tagged pyrrolidines is frequently reported.
Conclusions:
- Chiral ionic liquids, especially proline derivatives, are powerful tools for asymmetric Michael additions.
- The design of CILs can be tailored for specific induction modes and catalytic roles.
- The recyclability of CILs supports their application in green chemistry.
Keywords:
Chiral ionic liquidMichael additionasymmetric reactioncatalystschiral solventimidazole ionic liquidMore Related Videos
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