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Explotación de la química de los fosfonatos en la desaromatización mediada por metales: construcción estereoselectiva

F Christopher Pigge¹, John J Coniglio, Rashmi Dalvi

¹Department of Chemistry, University of Iowa, 305 Chemistry Building, Iowa City, Iowa 52242, USA. chris-pigge@uiowa.edu

Journal of the American Chemical Society

|March 16, 2006

Resumen

Los complejos de rutenio se someten a espirociclado para formar aductos estables. Este proceso permite la síntesis de derivados de decano enantioméricamente puros azaspiro [4.5] , mostrando capacidades de síntesis asimétricas.

Área de la Ciencia:

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

Sus antecedentes:

Los complejos de rutenio son catalizadores versátiles en la síntesis orgánica.
Los compuestos espirocíclicos poseen propiedades estructurales y biológicas únicas.
El desarrollo de métodos eficientes para la construcción de espirociclos es un desafío significativo.

Objetivo del estudio:

Desarrollar una nueva reacción de espirociclado intramolecular utilizando complejos de areno rutenio.
Para lograr la síntesis estereoselectiva de los aductos de rutenio ciclohexadienil.
Para permitir la conversión diastereoselectiva a los derivados de decano azaspiro[4.5] libres de metales.

Principales métodos:

Empleando complejos de areno rutenio con cadenas laterales de beta-amido fosfonato.
Utilizando una secuencia de dos pasos en tándem que involucra adición aromática nucleofílica y olefinación Horner-Wadsworth-Emmons.
Realizar la desmetalización oxidativa en presencia de nucleófilos para la formación de productos libres de metales.

Principales resultados:

Se han sintetizado con éxito aductos estables de ciclohexadienil rutenio.
La espirociclación procedió con una alta estereoselectividad.
Una espirociclación asimétrica produjo un solo enantiómero del producto espirolactam.
Se obtuvieron derivados de decano azaspiro[4.5] libres de metales con una alta diastereoselectividad.

Conclusiones:

El método desarrollado proporciona una ruta eficiente a complejas estructuras espirocíclicas.
Este enfoque es valioso para la síntesis asimétrica, produciendo compuestos enantioméricamente puros.
La metodología ofrece una estrategia versátil para acceder a diversos andamios de azaspiro[4.5]decane.

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