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Catalizador D2-simétrico de dirodio derivado de un ligando 1,2,2-triarilciclopropanocarboxilato: diseño, síntesis y

Changming Qin¹, Vyacheslav Boyarskikh, Jørn H Hansen

¹Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.

Journal of the American Chemical Society

|November 4, 2011

Resumen

Dirhodium tetrakis-{R}-{1-{4-bromofenil}-2,2-difenilciclopropanocarboxilato) (Rh{2}{R}-BTPCP) es un nuevo catalizador quiral para las ciclopropanaciones altamente enantioselectivas y las reacciones en tándem. Este catalizador ofrece facilidad de síntesis y compatibilidad con varios sustratos y disolventes.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
Catalización asimétrica por catálisis asimétrica.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

Los catalizadores quirales son esenciales para la síntesis enantioselectiva.
Los complejos de dirhodium son ampliamente utilizados en las reacciones de ciclopropanación.
El desarrollo de catalizadores quirales eficientes y versátiles sigue siendo un desafío clave en la química orgánica.

Objetivo del estudio:

Para evaluar la eficacia de Dirhodium tetrakis-{R}-{1-{4-bromofenil) -2,2-difenilciclopropanocarboxilato) (Rh{2}-{R}-BTPCP) {4)) como un catalizador quiral.
Explorar su aplicación en la ciclopropanación enantioselectiva y reacciones relacionadas.
Comprender el mecanismo catalítico a través de estudios computacionales.

Principales métodos:

Síntesis del catalizador quiral de dirodio Rh(2)(R-BTPCP)(4).
Reacciones enantioselectivas de ciclopropanación con el uso de acetatos de arilo y de estirilidio.
Ciclopropanación en tándem / reacciones de reordenamiento de Cope y funcionalización C-H / reacciones de reordenamiento de Cope.
Modelado computacional para dilucidar la estructura y el mecanismo del catalizador.

Principales resultados:

Rh-BTPCP) ha demostrado una alta enantioselectividad en las reacciones de ciclopropanación.
Logro exitoso de ciclopropanación en tándem/reorganizaciones de Cope y funcionalización C-H/reorganización de Cope.
El catalizador exhibe facilidad de síntesis, tolerancia al tamaño del grupo éster y compatibilidad con el diclorometano.
Los estudios computacionales revelaron la rotación dinámica del ligando para acomodar la unión al sustrato.

Conclusiones:

Rh2 (R-BTPCP) es un catalizador quiral altamente efectivo para varias transformaciones enantioselectivas.
Sus ventajas prácticas, incluida la síntesis y la compatibilidad, lo convierten en una herramienta valiosa para la síntesis orgánica.
La flexibilidad estructural del catalizador juega un papel crucial en su reactividad y selectividad.

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