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Desarrollo de ésteres biarylohemibóricos para la síntesis de atropisómeros de biarylo a través del acoplamiento

Yiming Yang¹, Changhui Wu¹, Junhao Xing¹

¹Department of Chemistry, School of Science, China Pharmaceutical University, Nanjing 211198, P. R. China.

Journal of the American Chemical Society

|February 21, 2024

Resumen

Desarrollamos un nuevo método usando ésteres biarilo-hemibóricos para la síntesis asimétrica de compuestos biarilo quirales. Esta reacción catalizada por el paladio ofrece una alta enantioselectividad y un amplio alcance de sustrato para crear moléculas complejas.

Área de la Ciencia:

Química orgánica
Síntesis asimétrica

Sus antecedentes:

Las estructuras biarílicas axialmente quirales son motivos importantes en los productos farmacéuticos y la ciencia de los materiales.
El desarrollo de métodos eficientes para su síntesis asimétrica sigue siendo un desafío clave en la química orgánica.

Objetivo del estudio:

Introducir los ésteres biarilohemibóricos como nuevos reactivos biarilo puenteados.
Desarrollar una reacción asimétrica de acoplamiento cruzado Suzuki-Miyaura catalizada por el paladio utilizando estos nuevos reactivos.

Principales métodos:

El estudio implica el desarrollo y la aplicación de reacciones asimétricas de acoplamiento cruzado Suzuki-Miyaura catalizadas por paladio.
Los ésteres biarylohemibóricos se emplearon como reactivos clave en un acoplamiento atroposelectivo dinámico.

Principales resultados:

El método desarrollado permite la síntesis asimétrica de estructuras biarílicas axialmente quirales con alta enantioselectividad.
La reacción demuestra una buena tolerancia funcional del grupo y un amplio alcance del sustrato.
Las aplicaciones sintéticas incluyen transformaciones de productos y la síntesis de poliarenos quirales.

Conclusiones:

Los ésteres biarylohemibóricos representan una nueva clase de reactivos biarylo puentes para la síntesis asimétrica.
El acoplamiento atroposelectivo dinámico catalizado por paladio es un método eficiente para construir compuestos biarílicos quirales.
Los estudios mecánicos sugieren que está involucrado un paso de transmitación atroposelectiva dinámica enantio-determinante.

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