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Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.

Synthesis and Decomposition Reactions

Synthesis and Decomposition Reactions

Synthesis and decomposition are two types of redox reactions. Synthesis means to make something, whereas decomposition means to break something. The reactions are accompanied by chemical and energy changes.

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A two step one-pot protocol for the umpolung of ketone enolates to enolonium species and addition of a nucleophile to the α-position is described. Nucleophiles include chloride, azide, azoles, allyl-silanes, and aromatic...

Alcohols from Carbonyl Compounds: Grignard Reaction

Alcohols from Carbonyl Compounds: Grignard Reaction

Grignard reagents are one of the most commonly used reagents used to synthesize alcohols from carbonyl compounds. Grignard reagents are organomagnesium halides with a highly polar carbon–magnesium bond. Due to the partial ionic nature of the C–Mg bond, the carbon functions as a strong nucleophile and attacks electrophiles like carbonyl carbon.
Magnesium from the reagent coordinates with carbonyl oxygen, further reducing the carbonyl carbon's electron density. Thus, the...

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Here, we present a protocol for the synthesis of two carbonyl-decorated carbenes. The protocol makes these interesting compounds readily available to chemists of all skill levels. In addition to the synthesis of these two carbenes, their use in the activation of white phosphorus is also...

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Related Experiment Video

Updated: Jan 20, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Direct Ether Synthesis Utilizing the Carbonyl Umpolung Reaction.

Isao Mizota¹, Miyuki Hotta¹, Ayaki Yamamoto¹

¹Department of Applied Chemistry, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan.

Organic Letters

|January 19, 2026

Summary

A novel one-step direct ether synthesis using Grignard reagents and α-ketoamides creates α-alkoxyamides. This carbonyl umpolung strategy also enables a tandem O-alkylation/aldol reaction for diastereoselective aldol products.

More Related Videos

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Related Experiment Videos

Last Updated: Jan 20, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Conventional ether synthesis often involves multiple steps and harsh conditions.
Developing efficient and direct methods for ether formation is crucial in organic synthesis.

Purpose of the Study:

To establish a direct, one-step synthesis of α-alkoxyamides.
To explore a novel application of carbonyl umpolung in O-alkylation.
To develop a tandem O-alkylation/aldol reaction for complex molecule synthesis.

Main Methods:

Treatment of α-ketoamides with Grignard reagents.
Utilizing carbonyl umpolung strategy for O-alkylation.
Performing tandem O-alkylation followed by aldol reaction with aldehydes.

Main Results:

Successful direct ether synthesis yielding α-alkoxyamides in good yields.
Demonstration of a one-step procedure superior to conventional methods.
Development of a tandem reaction affording aldol products with high diastereoselectivity.

Conclusions:

The developed method offers a simple and efficient route to α-alkoxyamides.
Carbonyl umpolung provides a powerful tool for O-alkylation.
The tandem reaction expands synthetic possibilities for constructing chiral molecules.