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Related Concept Videos

Conjugate Addition of Enolates: Michael Addition01:08

Conjugate Addition of Enolates: Michael Addition

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The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Ionic Radii03:10

Ionic Radii

33.6K
Ionic radius is the measure used to describe the size of an ion. A cation always has fewer electrons and the same number of protons as the parent atom; it is smaller than the atom from which it is derived. For example, the covalent radius of an aluminum atom (1s22s22p63s23p1) is 118 pm, whereas the ionic radius of an Al3+ (1s22s22p6) is 68 pm. As electrons are removed from the outer valence shell, the remaining core electrons occupying smaller shells experience a greater effective nuclear...
33.6K
Ionic Bonds00:42

Ionic Bonds

131.4K
Overview
When atoms gain or lose electrons to achieve a more stable electron configuration they form ions. Ionic bonds are electrostatic attractions between ions with opposite charges. Ionic compounds are rigid and brittle when solid and may dissociate into their constituent ions in water. Covalent compounds, by contrast, remain intact unless a chemical reaction breaks them.
Opposing Charges Hold Ions Together in Ionic Compounds
Ionic bonds are reversible electrostatic interactions between ions...
131.4K
Chirality02:25

Chirality

29.7K
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
29.7K
Molecular and Ionic Solids02:54

Molecular and Ionic Solids

20.2K
Crystalline solids are divided into four types: molecular, ionic, metallic, and covalent network based on the type of constituent units and their interparticle interactions.
Molecular Solids
Molecular crystalline solids, such as ice, sucrose (table sugar), and iodine, are solids that are composed of neutral molecules as their constituent units. These molecules are held together by weak intermolecular forces such as London dispersion forces, dipole-dipole interactions, or hydrogen bonds, which...
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Updated: Feb 9, 2026

Pretreatment of Lignocellulosic Biomass with Low-cost Ionic Liquids
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Asymmetric Michael Addition Mediated by Chiral Ionic Liquids.

Yumiko Suzuki1

  • 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
PubMed
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.

Keywords:
Chiral ionic liquidMichael additionasymmetric reactioncatalystschiral solventimidazole ionic liquid

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Synthesis of Bimetallic Pt/Sn-based Nanoparticles in Ionic Liquids
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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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.