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Funcionalización C-H enantioselectiva catalizada por rutenio: un acceso práctico a los derivados de indolina

Zhong-Yuan Li¹, Hetti Handi Chaminda Lakmal¹, Xiaolin Qian¹

¹Department of Chemistry , Mississippi State University , Mississippi State , Mississippi 39762 , United States.

Journal of the American Chemical Society

|September 20, 2019

Resumen

Este estudio introduce un nuevo método catalizado por rutenio para la activación enantioselectiva de C-H, que permite una síntesis eficiente de derivados quirales de indolina. El sistema catalítico desarrollado logra altos rendimientos y enantioselectividad para posibles aplicaciones farmacéuticas.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

La activación catalítica de C-H es una herramienta poderosa para la síntesis molecular.
La síntesis enantioselectiva de moléculas orgánicas complejas sigue siendo un desafío significativo.

Objetivo del estudio:

Desarrollar una nueva reacción de activación/hidroarilación C-H enantioselectiva catalizada por rutenio.
Para sintetizar derivados quirales de indolina con una alta enantioselectividad.

Principales métodos:

Se utilizan como catalizadores los complejos de Ru (II) areno disponibles en el mercado y las α-metilaminas quirales.
Empleó un grupo de dirección transitorio quiral esterilizado.
Se ha realizado la activación catalítica de C-H y la hidroarilación.

Principales resultados:

Se ha logrado una síntesis altamente enantioselectiva de derivados de la indolina.
Se obtienen indolinas multisubstituidas con un rendimiento de hasta el 92% y un exceso enantiomérico del 96% (ee).
Se ha demostrado una mayor transformación de la 4-formilindolina en un compuesto tricíclico ópticamente activo.

Conclusiones:

Se estableció la primera activación / hidroarilación enantioselectiva de C-H catalizada por Ru (II) para la síntesis de indolina.
El método desarrollado proporciona acceso a bloques de construcción quirales valiosos para aplicaciones farmacéuticas potenciales.

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