Video Experimental Relacionado

Updated: Jun 26, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Síntesis asimétrica de anillos de tamaño mediano por ciclopropanación catalizada por Au (I) intramolecular

Iain D G Watson¹, Stefanie Ritter, F Dean Toste

¹Department of Chemistry, University of California, Berkeley, California 94720, USA.

Journal of the American Chemical Society

|January 24, 2009

Resumen

Los investigadores desarrollaron un eficiente método asimétrico catalizado por oro para sintetizar anillos de tamaño mediano (de 7 a 9 miembros). Este enfoque logra altos rendimientos y excelentes enantioselectividades para anillos de 7 y 8 miembros, ofreciendo conocimientos mecanicistas.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis es la catálisis.
Síntesis asimétrica de síntesis.

Sus antecedentes:

Los anillos de tamaño mediano son objetivos sintéticos desafiantes.
Las reacciones catalizadas por oro ofrecen una reactividad única.
La catálisis asimétrica es crucial para los compuestos enantioméricamente puros.

Objetivo del estudio:

Desarrollar un método eficiente asimétrico catalizado por oro para la síntesis de anillos de tamaño mediano.
Para lograr altos rendimientos y enantioselectividades en la formación de anillos de 7 a 9 miembros.
Para obtener una comprensión mecanicista del proceso catalizado por el oro.

Principales métodos:

El oro asimétrico ((I) catálisis.
Reacciones de ciclización para formar anillos de tamaño mediano.
Uso de complejos de oro quiral.

Principales resultados:

Preparación eficiente de anillos de 7 a 9 miembros.
Se obtienen excelentes rendimientos para los tamaños de anillo objetivo.
Se obtienen altas enantioselectividades para productos de anillos de 7 y 8 miembros.
Conocimiento de la naturaleza fluxional de los intermediarios estabilizados con oro de vinilo carbenoide.

Conclusiones:

Se ha establecido un método nuevo y eficiente para la síntesis asimétrica de anillos de tamaño medio.
El método desarrollado es adecuado para producir compuestos cíclicos enriquecidos enantioméricamente.
Los estudios mecanicistas revelan detalles importantes sobre los intermediarios catalíticos.

Más Videos Relacionados

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Videos de Conceptos Relacionados

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.

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).

[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.

Base-Catalyzed Ring-Opening of Epoxides

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...

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...