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Catalysis

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.

Reactivity of Enols

Reactivity of Enols

Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is governed by factors like...

Regioselective Formation of Enolates

Regioselective Formation of Enolates

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.

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...

Stereochemical Effects of Enolization

Stereochemical Effects of Enolization

The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.

Catalysis

Catalysis

Catalysis influences the rate of chemical reactions by providing an alternative reaction pathway with lower activation energy. A catalyst speeds up a reaction, but it is not consumed during the process. The fundamental principle of catalysis is the ability of a catalyst to alter the reaction mechanism, often introducing a more efficient pathway than the uncatalyzed process.In a catalyzed reaction, the catalyst participates directly in the reaction mechanism. It interacts with reactants to form...

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Related Experiment Video

Updated: Jul 5, 2026

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

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

Published on: November 27, 2015

Catalytic enantioselective decarboxylative protonation.

Justin T Mohr¹, Toyoki Nishimata, Douglas C Behenna

¹Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

Journal of the American Chemical Society

|August 31, 2006

Summary

Researchers developed a catalytic method for creating chiral tertiary stereocenters in cyclic ketones. This process efficiently synthesizes substituted cycloalkanones with high enantioselectivity using beta-ketoesters.

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Last Updated: Jul 5, 2026

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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Published on: November 27, 2015

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Published on: January 17, 2020

Area of Science:

Organic Chemistry
Asymmetric Catalysis
Stereoselective Synthesis

Background:

Tertiary stereocenters are common motifs in pharmaceuticals and natural products.
Developing efficient methods for their asymmetric synthesis remains a significant challenge in organic chemistry.

Purpose of the Study:

To report a novel catalytic system for the enantioselective synthesis of tertiary stereocenters adjacent to cyclic ketones.
To establish a general and facile method for accessing substituted cycloalkanone compounds.

Main Methods:

Utilizing a catalytic decarboxylative protonation strategy.
Employing readily accessible racemic quaternary beta-ketoesters as substrates.
Applying the method to a range of substituted cycloalkanone precursors.

Main Results:

Achieved a highly enantioselective and general catalytic system.
Demonstrated facile synthesis of tertiary stereocenters.
Successfully synthesized various substituted cycloalkanone compounds with high enantioselectivity.

Conclusions:

The developed catalytic system offers an efficient route to enantiomerically enriched tertiary stereocenters in cyclic ketones.
This method provides a valuable tool for the synthesis of complex chiral molecules, including pharmaceutical intermediates.