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Síntesis diastereoselectiva de transalquenos de anillo de siete miembros a partir de dienos y aldehídos por

Margaret A Greene¹, Michel Prévost, Joshua Tolopilo

¹Department of Chemistry, New York University, New York, New York 10003, United States.

Journal of the American Chemical Society

|July 12, 2012

Resumen

La catálisis de plata permite la transferencia regioselectiva de silileno a los alquenos, creando vinilsilaciclopropanos. Estos intermediarios producen transalquenos de siete miembros a través de la adición a aldehídos, lo que demuestra una alta reactividad en las reacciones de reordenamiento y adición.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
Síntesis orgánica La síntesis orgánica.
La catálisis es la catálisis.

Sus antecedentes:

Las reacciones de transferencia de silileno son cruciales para la formación de compuestos orgánicos que contienen silicio.
Los vinilsilaciclopropanos son versátiles intermediarios en la síntesis orgánica.
El control de la estereoquímica en la formación de estructuras cíclicas complejas sigue siendo un desafío.

Objetivo del estudio:

Desarrollar un nuevo método catalizado por plata para la transferencia de sileno a alquenos.
Para investigar la reactividad posterior de los vinilsilaciclopropanos resultantes.
Para lograr la síntesis diastereoselectiva de transalquenos de siete miembros.

Principales métodos:

Reacción de transferencia de silileno catalizada por plata utilizando alquenos.
Reacciones de adición de silanos alilicos derivados de los vinilsilaciclopropanos a los aldehídos.
Análisis de los productos de reacción utilizando métodos espectroscópicos y análisis estereoquímico.

Principales resultados:

Formación regioselectiva de vinilsilaciclopropanos a partir de alquenos a través de la catálisis de la plata.
Alta diastereoselectividad en la formación de transalquenos de siete miembros a través de la adición de aldehídos.
Se ha demostrado una alta reactividad de los transalquenos en los reordenamientos [1,3]-sigmatrópicos y la adición de enlaces O-H.

Conclusiones:

La catálisis de plata proporciona una ruta eficiente hacia los vinilsilaciclopropanos.
Los vinilsilaciclopropanos sintetizados son valiosos precursores para complejos sistemas de anillos de siete miembros.
El estudio destaca la utilidad sintética y la reactividad de estos nuevos compuestos que contienen silicio.

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