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Carboeterificación intermolecular catalizada por el paladio de los dihidrofuranos

Gustavo M Borrajo-Calleja¹, Vincent Bizet¹, Clément Mazet¹

¹Department of Organic Chemistry, University of Geneva , 30 quai Ernest Ansermet, 1211 Geneva, Switzerland.

Journal of the American Chemical Society

|March 16, 2016

Resumen

Una nueva reacción catalizada por el paladio permite la síntesis de tetrahidrofurobenzofuranos fundidos. Este método enantioselectivo utiliza ligandos quirales generados in situ para un alto rendimiento y pureza.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Los dihidrofuranos son compuestos heterocíclicos muy versátiles.
Las reacciones catalizadas por paladio son ampliamente utilizadas en la síntesis orgánica.
La síntesis enantioselectiva es crucial para los productos farmacéuticos y los productos químicos finos.

Objetivo del estudio:

Desarrollar un nuevo método enantioselectivo para la carboeterificación de dihidrofuranos.
Establecer un sistema catalítico general para la síntesis de tetrahidrofurobenzofuranos fundidos.
Investigar la utilidad de los ligandos quirales de monóxido de bisfosfina generados in situ.

Principales métodos:

Enantioselectiva catalizada por el paladio para la carboeterificación intermolecular.
Generación in situ de ligandos quirales de monóxido de bisfosfina.
Síntesis de varios tetrahidrofurobenzofuranos fundidos

Principales resultados:

Se logró una nueva carboeterificación intermolecular enantioselectiva catalizada por Pd de los dihidrofuranos.
La generación in situ de ligandos quirales de monóxido de bisfosfina resultó crucial para el éxito de la reacción.
El sistema catalítico desarrollado proporcionó acceso a una gama de tetrahidrofurobenzofuranos fundidos.
Se obtuvieron rendimientos consistentemente altos y excesos enantioméricos.

Conclusiones:

Se ha establecido un sistema catalítico general y eficiente para la síntesis enantioselectiva de tetrahidrofurobenzofuranos fundidos.
La generación in situ de ligandos quirales es una estrategia clave para esta transformación.
Este método ofrece una ruta valiosa para moléculas quirales complejas.

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