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α-Alkylation of Ketones via Enolate Ions

α-Alkylation of Ketones via Enolate Ions

Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the strong interaction...

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

EDTA: Chemistry and Properties

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Polydentate ligands are most widely used in complexometric titrations because they form more stable complexes with the metal ions than mono- or bidentate ligands due to the chelate effect. Examples of polydentate ligands are ethylenediaminetetraacetic acid (EDTA), crown ethers, and cryptands. The most important feature of optimal polydentate ligands is the ability to form 1:1 complexes in a single-step process. Amino carboxylic acid derivatives are frequently used as complexing agents. EDTA is...

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Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate base is localized on the oxygen...

Regioselective Formation of Enolates

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As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.

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Related Experiment Video

Updated: Jun 13, 2026

Functional Characterization of Na+/H+ Exchangers of Intracellular Compartments Using Proton-killing Selection to Express Them at the Plasma Membrane

Functional Characterization of Na⁺/H⁺ Exchangers of Intracellular Compartments Using Proton-killing Selection to Express Them at the Plasma Membrane

Published on: March 30, 2015

Enantioselective protonation.

Justin T Mohr¹, Allen Y Hong, Brian M Stoltz

¹Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Department of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Mail Code 164-30, Pasadena, CA 91125, USA.

Nature Chemistry

|April 30, 2010

Summary

This summary is machine-generated.

Enantioselective protonation, crucial in biosynthesis, is now achievable through new chemical methods. These techniques offer valuable control for synthesizing organic compounds.

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Area of Science:

Organic Chemistry
Biochemistry
Synthetic Chemistry

Background:

Enantioselective protonation is a key step in many natural biosynthetic pathways.
Enzymes like decarboxylases and esterases control steric and proton environments for this transformation.
Developing synthetic analogs is essential for chemical synthesis.

Purpose of the Study:

To review recent advancements in chemical methods for enantioselective protonation.
To highlight the strategies employed for enantiocontrol in laboratory settings.
To underscore the utility of these methods in preparing valuable organic compounds.

Main Methods:

Exploitation of various enantiocontrol mechanisms in chemical reactions.
Development of novel catalytic systems for protonation.
Application of different proton donors and acceptors in synthetic designs.

Main Results:

Several chemical methods have been successfully developed to mimic enzymatic enantioselective protonation.
These methods provide effective control over the stereochemical outcome of protonation.
The transformations are applicable to the synthesis of diverse and valuable organic molecules.

Conclusions:

Chemical methods for enantioselective protonation have advanced significantly.
These synthetic approaches offer alternatives to natural enzymatic processes.
The developed methods are valuable tools for organic synthesis and drug discovery.