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Acoplamiento reductivo práctico y asimétrico de isoquinolinas plantilladas por diborones quirales

Dongping Chen¹, Guangqing Xu², Qinghai Zhou^3,4

¹School of Physical Science and Technology, ShanghaiTech University , Shanghai 200031, China.

Journal of the American Chemical Society

|July 13, 2017

Resumen

Los investigadores desarrollaron un nuevo método para sintetizar bisisoquinolinas quirales utilizando un acoplamiento reductivo de isoquinolinas. Este proceso eficiente ofrece una excelente estereoselectividad y una amplia aplicabilidad en condiciones suaves.

Área de la Ciencia:

Química orgánica
Síntesis asimétrica

Sus antecedentes:

Las isoquinolinas son compuestos heterocíclicos importantes con diversas aplicaciones.
El desarrollo de métodos eficientes para sintetizar isoquinolinas sustituidas quirales sigue siendo un desafío.

Objetivo del estudio:

Desarrollar un nuevo acoplamiento reductor quiral de isoquinolinas con plantilla de diboron.
Para lograr una síntesis altamente diastereoselectiva y enantioselectiva de las bisisoquinolinas quirales.

Principales métodos:

Se utilizó un catalizador quiral de diboron para modelar la reacción de acoplamiento reductivo.
La reacción involucró a las isoquinolinas como sustratos en condiciones suaves.

Principales resultados:

El método desarrollado proporcionó un acceso acelerado a las bisisoquinolinas sustituidas quirales.
La síntesis logró buenos rendimientos y excelentes excesos enantioméricos (ee).
La reacción demostró un amplio alcance del sustrato y una buena compatibilidad del grupo funcional.

Conclusiones:

El acoplamiento reductor con plantilla de diboron quiral es una estrategia eficaz para sintetizar bisisoquinolinas quirales.
Los estudios mecánicos sugieren una vía concertada de reordenamiento sigmatrópico [3,3].
Este método ofrece una herramienta valiosa para acceder a moléculas quirales complejas.

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