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Shen Gao¹, Lei Su¹, Jiawang Liu¹

¹Frontiers Science Center for Transformative Molecules, State Key Laboratory of Synergistic Chem-Bio Synthesis, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240 ,China.

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Resumen

Este estudio introduce una nueva reacción catalizada por el paladio para sintetizar óxidos quirales de fosfina con quiralidad axial y P. El método crea eficientemente atropisómeros complejos, superando un desafío clave en la síntesis asimétrica.

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Área de la Ciencia:

Química orgánica
Síntesis asimétrica
Catálisis

Sus antecedentes:

Los atropisómeros con quiralidad axial y P son valiosos pero difíciles de sintetizar.
Los métodos existentes para construir estas moléculas quirales son limitados.

Objetivo del estudio:

Desarrollar una síntesis asimétrica catalítica para atropisómeros con quiralidad axial y P.
Establecer una reacción de acoplamiento C-P catalizada por Pd para la construcción atroposelectiva de heterobiarilos estero-P.

Principales métodos:

Utilizó el acoplamiento C-P diastereoselectivo y enantioselectivo catalizado por el paladio.
Se ha empleado la transformación dinámica cinética asimétrica de los heterobiarilos.
Resolución cinética incorporada de óxidos de fosfina secundarios no simétricos.

Principales resultados:

Se ha logrado la síntesis atroposelectiva de heterobiarilos P-esterogénicos.
Se ha demostrado un amplio alcance de sustrato y una excelente tolerancia al grupo funcional.
Produjo diversos óxidos de fosfina axial y P-chiral en altos rendimientos y selectividades.

Conclusiones:

El protocolo desarrollado proporciona una ruta eficiente a los complejos óxidos quirales de fosfina.
El método permite la síntesis de valiosos ligandos y catalizadores quirales.
Este trabajo avanza en el campo de la síntesis asimétrica catalítica para los atropisómeros.