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Catalizado por rutenio ((II) [2 + 2 + 2] cicloadición de 1,6-diinas con compuestos tricarbonilo

Yoshihiko Yamamoto¹, Hideyuki Takagishi, Kenji Itoh

¹Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan.

Journal of the American Chemical Society

|June 13, 2002

Resumen

La catálisis del rutenio permite que las 1,6-diinas asimétricas reaccionen con los compuestos tricarbonilo, formando dienonas. La subsiguiente adición intramolecular de Michael produce complejos derivados de la biciclo[3.3.0]octenona.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Las 1,6-diinas son versátiles bloques de construcción en la síntesis orgánica.
Las reacciones catalizadas por rutenio ofrecen transformaciones selectivas.
Los compuestos tricarbonilo son sintones útiles para la construcción de moléculas complejas.

Objetivo del estudio:

Desarrollar una nueva ruta sintética para las dienonas y los derivados de la biciclo[3.3.0]octenona.
Para explorar la reactividad de las 1,6-diinas asimétricas con compuestos tricarbonilo con déficit de electrones.
Para investigar el papel catalítico de Cp*Ru(cod) Cl en esta transformación.

Principales métodos:

Reacción catalítica mediante el uso de Cp*Ru(cod)Cl.Cl.
Reacción de las 1,6-diinas asimétricas con los compuestos tricarbonilo con déficit de electrones.
Apertura del anillo electrocíclico y adición intramolecular de Michael.

Principales resultados:

Formación selectiva de dienonas a partir de compuestos de 1,6-diinas y tricarbonilo.
Síntesis de derivados de la biciclo[3.3.0]octenona a través de la adición intramolecular de Michael.
Demostración de la tolerancia del método a varios grupos funcionales.

Conclusiones:

Cp*Ru(cod) Cl cataliza efectivamente la reacción entre las 1,6-dinas y los compuestos tricarbonilo.
El método desarrollado proporciona acceso a valiosos andamios de dienona y biciclo[3.3.0]octenona.
Este trabajo amplía la utilidad sintética de 1,6-diines en cicloadiciones catalizadas por rutenio.

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