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Regioselective Formation of Enolates01:33

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

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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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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation01:14

Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation

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This lesson delves into the aldol condensation catalyzed by bases, where aldols undergo dehydration to enals. As shown in Figure 1, the β-hydroxy aldehyde formed in a base-catalyzed aldol addition reaction dehydrates on heating to yield an unsaturated carbonyl product, which is commonly referred to as an enal.
7.5K
Reactivity of Enols01:18

Reactivity of Enols

4.4K
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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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

4.9K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Efficient methods for enol phosphate synthesis using carbon-centred magnesium bases.

William J Kerr1, David M Lindsay, Vipulkumar K Patel

  • 1Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK. w.kerr@strath.ac.uk.

Organic & Biomolecular Chemistry
|September 29, 2015
PubMed
Summary

New methods efficiently convert ketones into kinetic enol phosphates using organomagnesium reagents. Optimized conditions yield high amounts of enol phosphates from various ketones, tolerating diverse functional groups.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry

Background:

  • Kinetic enol phosphates are valuable synthetic intermediates.
  • Previous methods for their synthesis often require harsh conditions or lack substrate scope.

Purpose of the Study:

  • To develop efficient and mild methods for synthesizing kinetic enol phosphates.
  • To explore the use of specific organomagnesium reagents for this transformation.

Main Methods:

  • Utilized di-tert-butylmagnesium and bismesitylmagnesium reagents.
  • Optimized the quench protocol for enol phosphate formation.
  • Investigated the reaction scope with various cyclohexanones and aryl methyl ketones.

Main Results:

  • Achieved efficient conversion of ketones to kinetic enol phosphates.
  • High yields of enol phosphates were obtained.
  • The developed method demonstrated tolerance for a range of functional groups.

Conclusions:

  • The developed organomagnesium-mediated methods provide a mild and accessible route to kinetic enol phosphates.
  • This approach offers a versatile strategy for synthesizing functionalized enol phosphates.