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Adición intermolecular enantioselectiva de aminas alifáticas a dienos acíclicos con un catalizador Pd-PHOX

Nathan J Adamson¹, Ethan Hull¹, Steven J Malcolmson¹

¹Department of Chemistry, Duke University , Durham, North Carolina 27708, United States.

Journal of the American Chemical Society

|April 29, 2017

Resumen

Este estudio introduce un nuevo método catalítico para la creación de aminas alilicas quirales a partir de materiales de partida simples. El proceso eficiente utiliza un catalizador de paladio y un ligando especial para una alta selectividad.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Los 1,3-dienos acíclicos son bloques de construcción versátiles en la síntesis orgánica.
La síntesis enantioselectiva de aminas alilicas sigue siendo un desafío significativo.
Las reacciones catalizadas por el paladio ofrecen herramientas poderosas para la formación de enlaces C-N.

Objetivo del estudio:

Desarrollar una adición intermolecular enantioselectiva catalítica de aminas alifáticas a 1,3-dienos acíclicos.
Para lograr altos rendimientos y enantioselectividades en condiciones suaves.
Investigar el papel de la estructura del ligando en la actividad y la selectividad del catalizador.

Principales métodos:

Se utilizó un catalizador de paladio complejo con un ligando de óxido de fosfina (PHOX).
Utilizan aminas alifáticas y 1,3-dienos acíclicos como sustratos.
Condiciones de reacción optimizadas, incluida la carga del catalizador (5 mol %) y la temperatura (temperatura ambiente o inferior).

Principales resultados:

Se ha logrado una síntesis eficiente de aminas alilicas con altas proporciones enantioméricas (hasta 97:3 er).
Se ha demostrado la eficacia del sistema catalizador Pd-PHOX para esta transformación.
Identificó el papel crítico de una fosfina con deficiencia de electrones en el ligando para mejorar la actividad y la selectividad del sitio.

Conclusiones:

Desarrolló un método robusto y eficiente para la síntesis enantioselectiva de aminas alilicas.
El sistema catalizador Pd-PHOX proporciona una herramienta valiosa para acceder a los productos de aminas quirales.
El diseño de ligandos es crucial para controlar tanto la actividad catalítica como la selectividad del sitio en la funcionalización de dienos.

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