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Las adiciones Michael enantioselectivas a las imidas alfa, beta insaturadas catalizadas por un complejo Salen-Al

Mark S Taylor¹, Eric N Jacobsen

¹Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.

Journal of the American Chemical Society

|October 14, 2005

Resumen

Un nuevo complejo de aluminio (Salen) cataliza eficientemente las reacciones de adición conjugada, creando valiosos compuestos multifuncionales. Este método permite la síntesis asimétrica de piperidinas enriquecidas enantioméricamente, incluida una ruta a la (-) -paroxetina.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis es la catálisis.
Síntesis asimétrica de síntesis.

Sus antecedentes:

Las reacciones de adición conjugada son cruciales para la formación de enlaces C-C.
El acceso a compuestos multifuncionales enriquecidos con enantio sigue siendo un desafío sintético.

Objetivo del estudio:

Desarrollar un sistema catalítico eficiente para la adición conjugada de nitriles.
Para sintetizar nuevos compuestos multifuncionales enriquecidos con enantio.
Para demostrar aplicaciones sintéticas en preparaciones farmacéuticas intermedias.

Principales métodos:

Utilizó un complejo de aluminio (Salen) como catalizador.
Adición conjugada realizada de nitriles di- y trisubstituidos a las imidas alfa, beta insaturadas.
Aplicado los productos en síntesis asimétrica de piperidinas.

Principales resultados:

El complejo de aluminio (Salen) demostró una alta eficiencia catalítica.
Se funcionalizó con éxito una amplia gama de imidas acíclicas sustituidas por alquilo y arilo.
Se sintetizaron piperidinas enriquecidas enantioméricamente, incluida una ruta a la (-) -paroxetina.

Conclusiones:

Se ha establecido una nueva metodología para la adición conjugada asimétrica de nitriles.
Este enfoque proporciona acceso a compuestos multifuncionales enriquecidos con enantio anteriormente inaccesibles.
La metodología es aplicable a la síntesis de bloques de construcción farmacéuticos valiosos.

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