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Estrategia dinámica de acoplamiento cruzado cinético para la síntesis asimétrica de heterobiarilos axialmente

Abel Ros¹, Beatriz Estepa, Pedro Ramírez-López

¹Instituto Investigaciones Químicas (CSIC-US), University of Seville , C/Américo Vespucio, 49, 41092 Sevilla, Spain.

Journal of the American Chemical Society

|October 11, 2013

Resumen

Un nuevo método de transformación asimétrica dinámica cinética (DYKAT) sintetiza piridinas quirales e isoquinolinas. Este acoplamiento catalizado por paladio utiliza materiales de partida racémicos para lograr una alta enantioselectividad en valiosos compuestos heterobiarilicos.

Área de la Ciencia:

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

Sus antecedentes:

La síntesis de las piridinas/isoquinolinas 2-arilo sustituidas por 2' y los heterobiarilos relacionados es crucial en la química medicinal.
Los métodos existentes a menudo carecen de eficiencia o enantioselectividad para andamios complejos de heterobiarilo.

Objetivo del estudio:

Desarrollar una nueva transformación dinámica cinética asimétrica (DYKAT) para la síntesis eficiente de 2-aril piridinas/isoquinolinas quirales 2'-sustituidas.
Para lograr una alta enantioselectividad en la síntesis de valiosos compuestos heterobiarilicos.

Principales métodos:

Se utilizó una reacción de acoplamiento catalizada por paladio ((0)).
Se emplean como sustratos 2-triflatos racémicos y boroxinas de arilo.
Incorpora un ligando de fosforamidita derivado de TADDOL para facilitar la transformación asimétrica.

Principales resultados:

Se han sintetizado con éxito las piridinas/isoquinolinas 2-arilo 2'-sustituidas y los heterobiarilos relacionados.
Se lograron buenas a excelentes enantioselectividades en los productos de acoplamiento.
Se ha demostrado la formación de configuración labile de adición oxidativa palladaciclos como un intermedio clave.

Conclusiones:

La técnica DYKAT desarrollada proporciona una ruta eficiente a los heterobiarilos enriquecidos enantioméricamente.
La metodología ofrece una herramienta valiosa para acceder a complejos derivados quirales de piridina e isoquinolina.
Comprender el mecanismo que involucra a los intermediarios del ciclo de la pala es clave para optimizar la reacción.

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