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Sin-carboaminación catalizada por el rodio de alquenos a través de un grupo directivo transitorio

Tiffany Piou¹, Tomislav Rovis¹

¹Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.

|October 28, 2015

Resumen

Este estudio introduce una nueva reacción catalizada por el rodio para la carboaminación de alquenos. Este método logra una síntesis estereoselectiva intermolecular sin precedentes de enlaces carbono-carbono y carbono-nitrógeno en un solo paso.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los alquenos son bloques de construcción procirales cruciales en la síntesis orgánica.
La difuncionalización de los alquenos es clave para crear estructuras moleculares complejas.
Las funcionalizaciones estereoselectivas de alceno existentes carecen de formación simultánea de enlaces carbono-nitrógeno.

Objetivo del estudio:

Desarrollar un nuevo método para la difuncionalización estereoselectiva intermolecular de alquenos.
Para lograr la formación simultánea de un enlace carbono-carbono y un enlace carbono-nitrógeno a través de un alqueno.
Establecer una nueva ruta sintética para las moléculas acíclicas que contienen aminas.

Principales métodos:

Carboaminación catalizada por el rodio de alquenos mediante el uso de enoxiftalimidas.
Generación in situ de un grupo de dirección de bidentados.
Utilización de un nuevo ligando ciclopentadienilo para el control de la reactividad.

Principales resultados:

El éxito de la carboaminación intermolecular y estereoselectiva de alquenos.
Formación sin precedentes de enlaces C-C y C-N a través de un alqueno en una sola reacción.
Demostró una nueva estrategia para sintetizar alquenos funcionalizados.

Conclusiones:

La reacción catalizada por rodio desarrollada ofrece una nueva vía para la difuncionalización de alceno.
Esta metodología permite la síntesis convergente y estereoselectiva de moléculas complejas que contienen aminas.
Los hallazgos amplían el conjunto de herramientas para la síntesis orgánica estereoselectiva.

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