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Published on: May 29, 2008
Estereoselectividad complementaria controlada por ligandos en la silaboración intramolecular catalizada por platino
Toshimichi Ohmura1, Hideki Furukawa, Michinori Suginome
1Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Journal of the American Chemical Society
|October 13, 2006
Resumen
Los catalizadores de platino permiten la silaboración intramolecular de éteres homoalilo para formar 1-oxa-2-silaciclopentanos. La elección del ligando dicta la estereoselectividad, logrando una alta selectividad trans o cis para diversas aplicaciones sintéticas.
Área de la Ciencia:
- Química organometálica Química orgánica de los metales.
- Química orgánica sintética y orgánica.
- La catálisis de la catálisis.
Sus antecedentes:
- Las reacciones intramoleculares son cruciales para una síntesis eficiente.
- La silaboración ofrece una vía para incorporar silicio en moléculas orgánicas.
- El control de la estereoquímica en las reacciones de ciclización sigue siendo un desafío clave.
Objetivo del estudio:
- Para desarrollar una silaboración intramolecular catalizada por platino de éteres de borilsilanilo homoalilo.
- Investigar la influencia de los ligandos de fósforo en la estereoselectividad de la ciclización.
- Para demostrar la utilidad sintética del método desarrollado.
Principales métodos:
- Utilizó catalizadores de platino para la silaboración intramolecular.
- Empleó varios ligandos de fósforo para ajustar el rendimiento del catalizador.
- Se analizaron los resultados estereoquímicos (proporciones trans/cis) utilizando técnicas como la espectroscopia de RMN.
- Sintetizó diastereómeros de 6-metilheptano-1,3,5-triol para mostrar su utilidad sintética.
Principales resultados:
- Se obtienen altos rendimientos de 1-oxa-2-silaciclopentanos a través de la silaboración intramolecular.
- Estereoselectividad dependiente de ligandos demostrada: el ligando PCyPh2 favoreció los transproductos (trans/cis = 81:19-92:8), mientras que el ligando tris(2,4-di-tert-butylphenyl) fosfito favoreció los cis-productos (trans/cis = 8:92-6:94).
- Se sintetizó con éxito un par de diastereómeros de 6-metilheptano-1,3,5-triol, confirmando el valor sintético del método.
Conclusiones:
- Desarrolló una eficiente silaboración intramolecular catalizada por platino para la síntesis de 1-oxa-2-silaciclopentanos.
- Se estableció una fuerte correlación entre la estructura del ligando de fósforo y el control estereoquímico en la ciclización.
- El método proporciona una ruta versátil a los compuestos que contienen silicio y moléculas complejas definidas estereocímicamente.
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