Video Experimental Relacionado

Updated: Mar 6, 2026

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

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

Published on: June 21, 2017

Diaminación asimétrica catalítica de los estirenos

Kilian Muñiz^1,2, Laura Barreiro¹, R Martín Romero¹

¹Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology , 16 Avgda. Països Catalans, 43007 Tarragona, Spain.

Journal of the American Chemical Society

|March 10, 2017

Resumen

Este estudio presenta un nuevo método para la diaminación catalítica enantioselectiva de los estirenos utilizando un catalizador quiral de yodo. El proceso respetuoso con el medio ambiente logra altos excesos enantioméricos (91-98%) para 30 ejemplos.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

La diaminación vicinal es una transformación crucial en la síntesis orgánica.
El desarrollo de métodos enantioselectivos para la diaminación sigue siendo un desafío.

Objetivo del estudio:

Informar de una diaminación catalítica enantioselectiva de los estirenos.
Para lograr esta transformación bajo control de reacción intermolecular.

Principales métodos:

Se utilizó un catalizador de ariliodina modificado quiralmente.
Operado dentro de un ciclo catalítico de yodo (I/III).
Se utiliza el ácido 3-cloroperbenzoico como oxidante terminal.
Se utilizó un sistema de disolvente ecológico.

Principales resultados:

Se ha demostrado el éxito de la diaminación catalítica enantioselectiva de los estirenos.
Se obtuvieron altos excesos enantioméricos (91-98%) en 30 ejemplos.
El proceso exhibió el control de la reacción intermolecular.

Conclusiones:

El método desarrollado ofrece una vía eficiente y enantioselectiva para la diaminación vicinal.
El uso de un catalizador quiral de yodo y disolventes benignos mejora el atractivo y la sostenibilidad del proceso.

Más Videos Relacionados

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

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

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

Published on: April 4, 2014

Videos de Conceptos Relacionados

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.