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El acoplamiento cruzado estereospecífico de las β-trifluoroboratoamidas de alquilo secundarias

Deidre L Sandrock¹, Ludivine Jean-Gérard, Cheng-yi Chen

¹Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.

Journal of the American Chemical Society

|November 17, 2010

Resumen

Los investigadores lograron un acoplamiento cruzado estereospecífico para compuestos de alquilo boro enriquecidos con enantio. La coordinación intramolecular previene la eliminación no deseada de beta-H, mejorando la selectividad del producto en esta reacción clave de síntesis orgánica.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química organometálica Química orgánica de los metales.
La catálisis de la catálisis.

Sus antecedentes:

Las reacciones estereospecíficas de acoplamiento cruzado son vitales para la construcción de moléculas orgánicas complejas.
Los compuestos secundarios de alquiboro no bencílicos son valiosos intermedios sintéticos pero sustratos difíciles para el acoplamiento cruzado.
La eliminación de beta-H es una vía común de competencia que reduce el rendimiento y la selectividad.

Objetivo del estudio:

Desarrollar un método de acoplamiento cruzado estereospecífico para compuestos de alquiboro secundario no bencílico enriquecidos con enantio.
Para superar el desafío de la eliminación de beta-H en tales reacciones de acoplamiento.
Permitir una síntesis eficiente de moléculas complejas con una estereoquímica definida.

Principales métodos:

Se utilizó la catálisis de paladio para la reacción de acoplamiento cruzado.
Se emplean como sustratos compuestos secundarios de alquilo boro no bencílicos enriquecidos con enantio.
Incorpora una estrategia de coordinación intramolecular que incluye un grupo carbonilo auxiliar.

Principales resultados:

Se logró con éxito el acoplamiento cruzado estereospecífico de los compuestos de alquilo boro objetivo.
Se ha demostrado una alta selectividad para la formación de productos, suprimiendo la vía de eliminación de beta-H.
La coordinación intramolecular dirigía efectivamente la vía de reacción.

Conclusiones:

El método desarrollado proporciona una ruta robusta para el acoplamiento cruzado estereospecífico de sustratos difíciles de alquilo boro.
La coordinación intramolecular es una poderosa estrategia para controlar la selectividad en la catálisis organometálica.
Este avance amplía el conjunto de herramientas para la síntesis asimétrica y la construcción de moléculas complejas.

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