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Diarilación asimétrica catalítica de estirenos y enamidas acíclicos internos

Yang Xi¹, Wenyi Huang¹, Chenchen Wang¹

¹Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.

Journal of the American Chemical Society

|April 28, 2022

Resumen

Este estudio introduce una nueva reacción catalizada por el paladio para la diarilación asimétrica de alquenos, creando valiosas moléculas quirales. El método sintetiza eficientemente carbamatos enriquecidos con enantio y derivados de aminas para posibles aplicaciones farmacéuticas.

Área de la Ciencia:

Química orgánica
Síntesis asimétrica
Catálisis

Sus antecedentes:

Las transformaciones enantioselectivas de olefinas son cruciales para la síntesis de compuestos orgánicos quirales.
El control de la quimioselectividad, la diastereoselectividad y la estereoselectividad en reacciones con alquenos acíclicos internos sigue siendo un desafío.

Objetivo del estudio:

Desarrollar una diarilación asimétrica regiodivergente catalizada por el paladio de tipo Heck de alceno acíclico interno.
Proporcionar un método simplificado para acceder a los carbamatos enriquecidos con enantio y a los derivados de aminas.

Principales métodos:

Diarilación asimétrica catalizada por el paladio de los carbamatos de cinamilo y las enamidas.
Se utilizan sales de diazonio y ácidos borónicos aromáticos como socios de acoplamiento.
Se emplean paladaciclos transitorios asistidos por coordinación de carbonilo para reacciones estereospecíficas.

Principales resultados:

Se ha logrado la 1,2-diarilación de alquenos, formando centros estereogénicos circundantes.
Se ha demostrado la diarilación migratoria asimétrica de las enamidas, creando estereocentros incontiguos a través de la caminata de la cadena 1,3.
Se han sintetizado carbamatos y derivados de aminas altamente funcionalizados, multisubstituidos y enantioenriquecidos.

Conclusiones:

El protocolo desarrollado ofrece un acceso eficiente a bloques de construcción quirales valiosos.
Los compuestos sintetizados son relevantes para los motivos biológicamente activos, ayudando potencialmente al descubrimiento de fármacos.

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