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Benzilación catalítica enantioselectiva directa a partir de ácidos acéticos de arilo

Patrick J Moon¹, Zhongyu Wei¹, Rylan J Lundgren¹

¹Department of Chemistry , University of Alberta , Edmonton , Alberta T6G 2G2 , Canada.

Journal of the American Chemical Society

|November 20, 2018

Resumen

Este estudio introduce un nuevo método catalizado por metales para la benzilación enantioselectiva utilizando ácidos acéticos de arilo. La reacción evita bases fuertes, lo que permite una compatibilidad de grupo funcional más amplia en la síntesis orgánica.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La benzilación enantioselectiva tradicional a menudo requiere nucleófilos muy básicos.
Estas condiciones limitan la compatibilidad de los grupos funcionales y el alcance del sustrato.

Objetivo del estudio:

Desarrollar una nueva reacción de benzilación enantioselectiva catalizada por metales.
Para permitir el uso directo de ácidos acéticos de arilo como precursores.
Para lograr una amplia tolerancia de grupo funcional.

Principales métodos:

Reacción catalizada por metales de electrófilos alilicos con ácidos acéticos de arilo.
La descarboxilación como el paso terminal después de la formación de enlaces C-C estereoselectivos.

Principales resultados:

Benzilación enantioselectiva exitosa directamente de los ácidos acéticos de arilo.
Demostración de una vía descarboxilada que permite condiciones de reacción suaves.
Se ha logrado una amplia compatibilidad de los grupos funcionales, superando los métodos existentes.

Conclusiones:

El método desarrollado ofrece una vía nueva y eficiente para la benzilación enantioselectiva.
El mecanismo descarboxilativo amplía la aplicabilidad de las reacciones de benzilación en la síntesis de moléculas complejas.

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