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Acoplamiento cruzado reductor enantioselectivo catalizado por níquel de las aziridinas de estirenilo

Brian P Woods¹, Manuel Orlandi², Chung-Yang Huang¹

¹Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society

|April 14, 2017

Resumen

Este estudio introduce una reacción catalizada por níquel que acopla las aziridinas de estirenilo y los yoduros de arilo. El método produce eficientemente 2-arilfenetilaminas enriquecidas con enantio a partir de materiales de partida racémicos.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Las reacciones de acoplamiento cruzado reductivo son cruciales para la formación de enlaces C-C.
El desarrollo de métodos eficientes para sintetizar aminas quirales sigue siendo un desafío importante en la química orgánica.

Objetivo del estudio:

Para reportar una nueva reacción de acoplamiento reductivo catalizado por níquel.
Para obtener una síntesis asimétrica de 2-arilfenetilaminas a partir de aziridinas de estirenilo y yoduros de arilo.
Investigar los factores que influyen en la enantioselectividad en el sistema catalítico.

Principales métodos:

Reacción de acoplamiento cruzado reductor catalizado por níquel.
Utilizando como sustratos aziridinas de estirenilo y yoduros de arilo.
El uso de un ligando quiral de bioxazolina para la catálisis asimétrica.
Análisis del mecanismo de reacción estereoconvergente.

Principales resultados:

Acoplamiento exitoso de las aziridinas de estirenilo con yoduros de arilo utilizando un catalizador de níquel.
Se obtiene una alta enantioselectividad en la formación de 2-arilfenetilaminas a partir de aziridinas racémicas.
Demostración de una vía de reacción estereoconvergente.
Identificación de la polarizabilidad del ligando como un factor clave para la enantioselectividad.

Conclusiones:

Se ha desarrollado un método estereoselectivo y eficiente para sintetizar 2-arilfenetilaminas enriquecidas con enantio.
El estudio pone de relieve el potencial de los ligandos quirales de la bioxazolina en la catálisis asimétrica del níquel.
La comprensión de los factores que rigen la enantioselectividad proporciona información para el diseño de futuros sistemas catalíticos.

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