Video Experimental Relacionado

Updated: Jun 27, 2025

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

Funcionalización enantioselectiva divergente catalizada por el paladio de los ciclobutenos

Zhonggui Wang¹, Jie Zhu², Minyan Wang²

¹Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, China.

Journal of the American Chemical Society

|April 27, 2024

Resumen

Este estudio introduce un nuevo método catalizado por el paladio para la síntesis de derivados del ciclo butano enriquecidos con enantio de los ciclo butanos. El enfoque permite diversos patrones estructurales, valiosos para aplicaciones químicas medicinales.

Área de la Ciencia:

Química orgánica
Química medicinal
Catálisis

Sus antecedentes:

Los anillos tensados alifáticos ofrecen propiedades fisicoquímicas y farmacocinéticas ventajosas para el desarrollo de fármacos.
La síntesis de derivados de ciclo butano enriquecidos con enantio con estructuras diversas sigue siendo un reto sintético.

Objetivo del estudio:

Desarrollar una nueva desimetrización enantioselectiva catalizada por el paladio de los ciclobutenos.
Acceso a diversos productos de hidroarilación y diarilación a partir de un intermediario común.

Principales métodos:

Desimetrización enantioselectiva catalizada por el paladio de los ciclobutenos.
Interceptación de un intermediario común de Heck para reacciones secuenciales.
Estudios mecánicos en los que se utiliza el etiquetado con deuterio.

Principales resultados:

Síntesis exitosa de derivados de ciclobutano enriquecidos con enantio a través de la hidroarilación y la diarilación.
Identificación de un intermediario común de Heck que rige la formación del producto.
Conocimientos sobre el comportamiento del catalizador de paladio y las variaciones de reacción sensibles al deuterio.

Conclusiones:

El método desarrollado proporciona un acceso eficiente a valiosos andamios de ciclo butano enriquecidos con enantio.
Utilidad demostrada en la síntesis de análogos de fármacos deuterados y arquitecturas moleculares complejas.

Más Videos Relacionados

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Videos de Conceptos Relacionados

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.

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

[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.

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.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).