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Enantioface selectiva de la silaboración catalizada por el paladio de los alenos a través de doble inducción

Michinori Suginome¹, Toshimichi Ohmura, Yoshihiro Miyake

¹Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, and PRESTO, Japan Science and Technology Corporation (JST), Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. suginome@sbchem.kyoto-u.ac.jp

Journal of the American Chemical Society

|October 14, 2005

Resumen

Los investigadores sintetizaron beta-borilolilsilanos enriquecidos con enantio utilizando un catalizador de paladio y un auxiliar quiral. Este método logró una alta estereoselectividad, ofreciendo una nueva ruta para los compuestos quirales de organosilicio.

Área de la Ciencia:

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

Sus antecedentes:

Los compuestos quirales orgánicos de silicio son bloques de construcción valiosos en la síntesis orgánica.
Desarrollar métodos eficientes para su síntesis estereoselectiva sigue siendo un desafío.

Objetivo del estudio:

Desarrollar un nuevo método catalizado por el paladio para la síntesis de enantioenriquecidos beta-borilolilsilanos.
Explorar el uso de auxiliares quirales en reacciones asimétricas de adición de enlaces silicio-boro.

Principales métodos:

Palladio catalizado enantio superficie-adición selectiva de enlaces de silicio-boro a los allenos terminales.
Utilizó un catalizador de paladio con un ligando quiral monodentado de fosfina.
Se emplean sililboranos con un auxiliar quiral en el átomo de boro.

Principales resultados:

Con éxito sintetizó enantio enriquecido con beta-borilolilsilanos.
Se han logrado elevadas selectividades enantioface, hasta un 96% de des.
Demostró la efectividad del auxiliar quiral en el control de la estereoquímica.

Conclusiones:

La reacción catalizada por el paladio desarrollada proporciona una ruta eficiente a las beta-borillallylsilanas quirales.
El uso de un auxiliar quiral es crucial para lograr una alta estereoselectividad.
Esta metodología amplía el conjunto de herramientas para la síntesis asimétrica de compuestos orgánicos de silicio.

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