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Acoplamiento asimétrico de tres componentes catalizado con paladio de ésteres de boro, indoles y acetato de alilo

Santanu Panda¹, Joseph M Ready¹

¹Department of Biochemistry, UT Southwestern Medical Center , Dallas, Texas 75390, United States.

Journal of the American Chemical Society

|April 18, 2017

Resumen

Este estudio introduce una nueva reacción de acoplamiento de tres componentes para sintetizar indolos y indolinas sustituidos. El proceso une de manera eficiente los acetatos alílicos, los indoles y los compuestos organoboron con alta selectividad.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los indolos y las indolinas son andamios heterocíclicos cruciales en la química medicinal.
El desarrollo de rutas sintéticas eficientes para los indoles funcionales sigue siendo un desafío clave.

Objetivo del estudio:

Desarrollar una nueva reacción de acoplamiento de tres componentes para la síntesis de indol e indolina.
Para lograr una alta enantio-, regio- y diastereoselectividad en el proceso de acoplamiento.

Principales métodos:

Reacción de ésteres borónicos con indoles 2-litiados para formar intermedios de boronato.
El acoplamiento catalizado por el paladio de los boronatos con los acetatos alílicos mediante catalizadores (BINAP) Pd.

Principales resultados:

Acoplamiento exitoso de tres componentes de acetato de alilo, indoles y especies de organoboron.
Formación de indolos y indolinas sustituidos con un excelente control estéreo.
Demostración de la alilación C3 y la migración de alquilo B a C2.

Conclusiones:

El método desarrollado proporciona una vía versátil y altamente selectiva para los derivados complejos de indol e indolina.
Este enfoque ofrece ventajas significativas para acceder a compuestos heterocíclicos definidos estereoquímicamente.

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