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Resolución cinética de quinolinas 5- o 8- sustituidas axialmente por transferencia asimétrica de hidrogenación
Jie Wang1,2, Mu-Wang Chen1, Yue Ji1
1State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, P. R. China.
Journal of the American Chemical Society
|August 13, 2016
Resumen
Los investigadores desarrollaron una resolución cinética eficiente para los derivados de quinolina axialmente quirales utilizando la hidrogenación de transferencia asimétrica. Este método creó con éxito dos esqueletos quirales con alta selectividad, marcando una primicia para los compuestos heteroaromáticos.
Área de la Ciencia:
- Química orgánica
- Síntesis asimétrica
- Catálisis
Sus antecedentes:
- Los biarilos axialmente quirales y los compuestos relacionados son motivos estructurales cruciales en los productos farmacéuticos y la ciencia de los materiales.
- El desarrollo de métodos eficientes para la síntesis y resolución de compuestos quirales enantioméricamente puros sigue siendo un desafío importante en la química orgánica.
Objetivo del estudio:
- Desarrollar un método de resolución cinética eficiente para sintetizar derivados de quinolina quiralmente sustituidos por 5 o 8 enantioméricamente enriquecidos.
- Explorar la aplicación de la hidrogenación por transferencia asimétrica en la resolución cinética de los compuestos heteroaromáticos.
Principales métodos:
- Resolución cinética de los derivados de quinolina axialmente racémica mediante la hidrogenación de transferencia asimétrica de la fracción heteroaromática.
- Utilizó un sistema de catalizador quiral para hidrogenar selectivamente un enantiómero sobre el otro.
Principales resultados:
- Se ha logrado una resolución cinética eficiente de los derivados de quinolina quirales axialmente.
- Se obtuvieron con éxito dos tipos distintos de esqueletos axialmente quirales con alta enantioselectividad (hasta 209 de factor de selectividad).
- Demostró la primera aplicación exitosa de la hidrogenación de transferencia asimétrica para la resolución cinética de biarilos axialmente quirales que involucran sistemas heteroaromáticos.
Conclusiones:
- El método de hidrogenación de transferencia asimétrica desarrollado proporciona una ruta efectiva para la resolución cinética de los derivados de quinolina axialmente quirales.
- Este estudio amplía el alcance de la hidrogenación por transferencia asimétrica al desafiante área de la resolución cinética heteroaromática, ofreciendo una herramienta valiosa para acceder a compuestos enantiopuros.
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