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Cicloadición enantioselectiva de benzociclobutenona y cetol catalizada por rutenio: fusión de activación de enlaces

Brett R Ambler¹, Ben W H Turnbull¹, Sankar Rao Suravarapu¹

¹University of Texas at Austin , Department of Chemistry , Austin , Texas 78712 United States.

Journal of the American Chemical Society

|July 12, 2018

Resumen

Los investigadores desarrollaron una nueva reacción de cicloadición enantioselectiva utilizando un catalizador de rutenio. Este método crea eficientemente moléculas complejas, incluida una parte clave del producto natural arenimicina.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis de productos naturales

Sus antecedentes:

Las benzociclobutenonas son productos intermedios sintéticos versátiles.
Las cicloadiciones enantioselectivas son cruciales para sintetizar moléculas quirales.
La formación de enlaces C-C catalizados por el metal ofrece rutas sintéticas eficientes.

Objetivo del estudio:

Describir la primera cicloadición enantioselectiva intermolecular catalizada por metales de las benzociclobutenonas.
Desarrollar un método para la construcción de estructuras policíclicas complejas con alto estereocontrol.
Para sintetizar la subestructura de la "región de la bahía" de arenimicina.

Principales métodos:

Se utilizó un complejo de rutenio con (R) -DM-SEGPHOS como catalizador.
Se empleó una estrategia de cicloadición intermolecular a través de la adición oxidativa de enlaces C-C.
Los cetoles derivados de tetralona reaccionaron con las benzociclobutenonas.

Principales resultados:

Logró la primera cicloadición enantioselectiva intermolecular catalizada por metales de las benzociclobutenonas.
Se ha demostrado una completa regioselectividad y diastereoselectividad en la formación del conducto de carga.
Se obtuvo una alta enantioselectividad utilizando el método catalizado por rutenio desarrollado.
Con éxito sintetizó la "región de la bahía" de la arenimicina.

Conclusiones:

La cicloadición catalizada por rutenio desarrollada es una herramienta poderosa para la síntesis enantioselectiva.
Este método proporciona un acceso eficiente a las arquitecturas moleculares complejas.
La síntesis de la subestructura de la arenimicina destaca la utilidad de esta nueva reacción.

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