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Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

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

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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.
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Types of Enols and Enolates01:19

Types of Enols and Enolates

4.0K
Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is undetectable for acetaldehyde, present as only 1.5 × 10−4 % of acetone, and present as only 1.2% of cyclohexanone. Two kinds of regioisomeric enols are possible for unsymmetrical ketones, and their net composition is 1% at equilibrium. This instability is due to the lower bond energy of C=C than the C=O group. The additional...
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Reactivity of Enols01:18

Reactivity of Enols

4.5K
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...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
7.8K
Nomenclature of Secondary and Tertiary Amines01:12

Nomenclature of Secondary and Tertiary Amines

5.7K
The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...
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Updated: Apr 17, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Exploring tertiary enamides as versatile synthons in organic synthesis.

Mei-Xiang Wang1

  • 1MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing 100080, China. wangmx@mail.tsinghua.edu.cn.

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Summary

Tertiary enamides, once considered stable, are now recognized for their enhanced reactivity. Controlling their electronic structure unlocks potent nucleophilic reactions for synthesizing valuable compounds.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Tertiary enamides were traditionally viewed as stable and less reactive enamine derivatives.
  • Recent research challenges this perspective by demonstrating methods to enhance their synthetic utility.

Purpose of the Study:

  • To summarize recent advancements in the nucleophilic reactions of tertiary enamides.
  • To highlight their applications in synthesizing biologically relevant natural products and heterocycles.

Main Methods:

  • Regulation of the cross-conjugation system in tertiary enamides.
  • Enhancing delocalization of nitrogen lone-pair electrons.

Main Results:

  • Successfully reinvigorated enaminic reactivity of tertiary enamides.
  • Demonstrated applications in natural product synthesis.
  • Showcased utility in creating heterocyclic compounds with pharmaceutical relevance.

Conclusions:

  • Tertiary enamides possess significant, tunable reactivity.
  • Their nucleophilic reactions offer a powerful tool for complex molecule synthesis.