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Hidrogenación asimétrica homogénea catalizada por el rodio de los derivados del naftol

Shu-Xin Zhang¹, Linhong Long^2,3, Zeyu Li^1,3

¹National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, P. R. China.

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|January 29, 2025

Resumen

La hidrogenación asimétrica de los derivados de naftol ahora es posible utilizando catalizadores atados de rodio-diamina. Este avance permite la síntesis de alto rendimiento de tetrahidronaftoles ópticamente puros, cruciales para los medicamentos intermedios quirales.

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Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

La hidrogenación asimétrica de derivados de naftol a tetrahidronaftoles presenta desafíos significativos debido al control de la aromaticidad y la selectividad.
El desarrollo de sistemas catalíticos eficientes para la reducción enantioselectiva de naftos es fundamental para la síntesis de productos farmacéuticos intermedios quirales.

Objetivo del estudio:

Informar sobre la primera hidrogenación asimétrica homogénea de derivados de naftol utilizando catalizadores atados de rodio y diamina.
Para lograr altos rendimientos y excelentes regio-, quimio- y enantioselectividades en la síntesis de 1,2,3,4-tetrahidronaftoles ópticamente puros.

Principales métodos:

Se utilizan catalizadores atados de rodio-diamina para la hidrogenación asimétrica homogénea.
Estudios mecanicistas empleados, incluidos enfoques experimentales y computacionales, para dilucidar la vía de reacción.
Se investigó el papel del 1,1,1,3,3-hexafluoroisopropanol (HFIP) como disolvente fluorado.

Principales resultados:

Se obtienen altos rendimientos (hasta el 98%) y excelentes enantioselectividades (>99% ee) para una amplia gama de 1,2,3,4-tetrahidronaftoles de pureza óptica.
Demostró que el HFIP desempeña un papel vital en el control de la reactividad y la selectividad.
Propuso un nuevo modo de activación sinérgica que involucra HFIP, hidrógeno y naftol, lo que lleva a la reducción de un tautómero ceto fugaz.

Conclusiones:

Desarrolló un protocolo sencillo y práctico para la hidrogenación asimétrica de derivados de naftol.
El método proporciona acceso a los intermediarios clave para los fármacos quirales, incluida la síntesis enantioselectiva de Nadolol.
Los hallazgos ofrecen un avance significativo en la síntesis asimétrica catalítica y la química farmacéutica.