Jove
Visualize
Contáctanos
JoVE
x logofacebook logolinkedin logoyoutube logo
ACERCA DE JoVE
Visión GeneralLiderazgoBlogCentro de Ayuda JoVE
AUTORES
Proceso de PublicaciónConsejo EditorialAlcance y PolíticasRevisión por ParesPreguntas FrecuentesEnviar
BIBLIOTECARIOS
TestimoniosSuscripcionesAccesoRecursosConsejo Asesor de BibliotecasPreguntas Frecuentes
INVESTIGACIÓN
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchivo
EDUCACIÓN
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualCentro de Recursos para ProfesoresSitio de Profesores
Términos y Condiciones de Uso
Política de Privacidad
Políticas

Videos de Conceptos Relacionados

Stereochemical Effects of Enolization01:12

Stereochemical Effects of Enolization

2.0K
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.
2.0K
Reactivity of Enols01:18

Reactivity of Enols

2.9K
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...
2.9K
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

2.5K
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.
2.5K
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

3.2K
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...
3.2K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.2K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.2K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

3.3K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
3.3K

También podría leer

Artículos Relacionados

Artículos vinculados a este trabajo por autores compartidos, revista y gráfico de citas.

Ordenar por
Same author

Vicinal disubstitution of alkyl C-X synthons via alkene radical cation generation.

Science (New York, N.Y.)·2026
Same author

Female reproductive impacts of emerging cyanobacterial harmful algal bloom toxins.

The Journal of reproduction and development·2026
Same author

Discovery and analytical assessment of urinary miRNA biomarkers for cervical cancer using advanced small RNA sequencing.

Translational oncology·2026
Same author

Copper-catalysed site-selective arylation of pyrazoles.

Nature chemistry·2026
Same author

Genetic Characterization and Zoonotic Potential of <i>Cryptosporidium</i> spp. and <i>Giardia duodenalis</i> in Cattle From Northeast China.

Transboundary and emerging diseases·2026
Same author

Photoredox-Neutral Platform for Direct Decarboxylative Cyclopropanation <i>via</i> Acridine-Iron Dual Catalysis.

ACS catalysis·2026

Video Experimental Relacionado

Updated: May 19, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.3K

Hidroacilación dinámica cinética asimétrica: Racemización por enolización suave

Mengfei Xu1, Stephanie A Corio2, Josephine M Warnica1

  • 1Department of Chemistry, University of California, Irvine, California 92697, United States.

Journal of the American Chemical Society
|April 29, 2025
PubMed
Resumen

Este estudio introduce una transformación cinética asimétrica dinámica (DyKAT) para crear 1,4-cetoamidas valiosas a partir de aldehídos. La hidroacilación catalizada por Rh logra una alta selectividad, ofreciendo una nueva estrategia de formación de enlaces C-C estereoconvergentes.

Más Videos Relacionados

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
06:31

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

8.8K
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

12.9K

Videos de Experimentos Relacionados

Last Updated: May 19, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.3K
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
06:31

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

8.8K
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

12.9K

Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis asimétrica

Sus antecedentes:

  • La transformación cinética asimétrica dinámica (DyKAT) permite la conversión de los materiales de partida racémicos en productos enriquecidos enantioméricamente.
  • La hidroacilación intermolecular es una poderosa reacción de formación de enlaces C-C, pero su aplicación en DyKAT sigue siendo poco explorada.
  • La catálisis estereoconvergente tiene como objetivo maximizar la eficiencia de la síntesis quiral mediante la conversión de múltiples estereocentros simultáneamente.

Objetivo del estudio:

  • Desarrollar una nueva transformación cinética asimétrica dinámica (DyKAT) para la síntesis enantioselectiva de 1,4-cetoamidas.
  • Para investigar la hidroacilación intermolecular catalizada por Rh de los aldehídos racémicos con las acrilamidas.
  • Para aclarar el mecanismo, incluida la vía de racemiación del aldehído, utilizando DFT y estudios experimentales.

Principales métodos:

  • Transformación asimétrica cinética dinámica (DyKAT)
  • Hidroacilación catalizada por el rodio
  • Reacción intermolecular
  • Cálculos del DFT
  • Resolución cinética

Principales resultados:

  • DyKAT exitoso de aldehídos racémicos con acrilamidas utilizando el catalizador Rh.
  • Se obtiene una alta enantio y diastereoselectividad en la formación de 1,4-cetoamidas.
  • Identificación de una inesperada vía catalizada por el Rh para la racemicidad del aldehído.
  • Demostración de una resolución cinética pionera a través de la hidroacilación intermolecular.

Conclusiones:

  • Este trabajo establece un nuevo DyKAT para sintetizar 1,4-cetoamidas con un excelente control estéreo.
  • Los hallazgos contribuyen significativamente al campo de la catálisis estereoconvergente y la construcción de enlaces C-C.
  • Los conocimientos mecanicistas proporcionan una base para el desarrollo de sistemas catalíticos relacionados.