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Hidrogenación asimétrica y completa de indoles y benzofuranos catalizados por Ru-NHC: un catalizador con doble

Fuhao Zhang¹, Himadri Sekhar Sasmal¹, Constantin G Daniliuc¹

¹Westfälische Wilhelms-Universität Münster Organisch-Chemisches Institut, Corrensstrasse 36, 48149 Münster, Germany.

Journal of the American Chemical Society

|July 12, 2023

Resumen

Un nuevo método permite la hidrogenación altamente enantioselectiva de indolos y benzofuranos, creando moléculas quirales esenciales para productos farmacéuticos y catalizadores. Este complejo de carbenos heterocíclicos de rutenio actúa como catalizador tanto homogéneo como heterogéneo.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Los octahidroindoles quirales y los octahidrobenzofuranos son componentes esenciales de los productos farmacéuticos y de los organocatalisadores.
El desarrollo de métodos eficientes para sintetizar estos andamios quirales es de gran interés.

Objetivo del estudio:

Desarrollar un método de hidrogenación altamente enantioselectivo y completo para los indoles y benzofuranos protegidos.
Explorar el uso de un complejo de carbenos heterocíclicos de rutenio como catalizadores tanto homogéneos como heterogéneos para la hidrogenación asimétrica.

Principales métodos:

Hidrogenación de indoles y benzofuranos protegidos mediante el uso de un complejo de carbenos heterocíclicos de rutenio.
Investigación del rendimiento del catalizador tanto en modos homogéneos como heterogéneos.
Caracterización de los octahidroindoles y octahidrobenzofuranos quirales resultantes.

Principales resultados:

Se logra una hidrogenación altamente enantioselectiva y completa de los indoles y benzofuranos protegidos.
Con éxito sintetizó una gama de octahidroindoles tridimensionales quirales y octahidrobenzofuranos.
Demostró la versatilidad del complejo de carbenos heterocíclicos de rutenio como catalizadores homogéneos y heterogéneos.

Conclusiones:

Desarrolló un método fácil para acceder a valiosas moléculas quirales.
El complejo de carbenos heterocíclicos de rutenio N es prometedor para la hidrogenación asimétrica de compuestos aromáticos difíciles.
Este trabajo abre nuevas vías para el diseño y la aplicación de catalizadores en síntesis asimétrica.

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