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La resolución de los complejos catiónicos (eta6-areno) tricarbonylmanganese quirales planas de los complejos de
Antoine Eloi1, Françoise Rose-Munch, Eric Rose
1UPMC Univ Paris 06, IPCM, CNRS UMR 7201, Equipe Chimie Organique et Organometallique, Case 181, 4 Place Jussieu, F-75005 Paris, France.
Journal of the American Chemical Society
|September 19, 2009
Resumen
Este estudio introduce un nuevo método para la resolución de complejos catiónicos (eta(6) -areno) Mn ((CO) ((3) utilizando un auxiliar quiral. Esta técnica innovadora permite la síntesis de compuestos enantiopuros, abriendo nuevas vías en la síntesis asimétrica.
Área de la Ciencia:
- Química organometálica Química orgánica de los metales.
- Síntesis asimétrica de síntesis.
- Resolución chiral de la resolución.
Sus antecedentes:
- Los complejos catiónicos (eta(6) -areno) Mn ((CO) ((3) son importantes intermediarios sintéticos.
- El desarrollo de métodos eficientes para la resolución quiral de estos complejos es crucial para la síntesis asimétrica.
Objetivo del estudio:
- Establecer un método novedoso y eficiente para la resolución quiral de complejos catiónicos (eta(6) -arenos) Mn ((CO) ((3).
- Para demostrar la utilidad de este método en la síntesis de moléculas orgánicas enantiopuras.
Principales métodos:
- Utilizado enolato de d-(+) -cánfora como nucleófilo quiral para la adición al complejo (eta(6) -areno) Mn ((CO) ((3).
- Se realizó la isomerización del centro estereogénico y se separaron los diastereoisómeros eta(5) resultantes.
- Se logró la rearomatización y la eliminación del auxiliar quiral para producir complejos resueltos.
Principales resultados:
- Se resolvieron con éxito los complejos catiónicos (eta(6) -areno) Mn ((CO) ((3) por primera vez utilizando este método.
- Demostró una secuencia general de adición/eliminación de nucleófilos quirales "ida y vuelta".
- Demostró la compatibilidad con los grupos funcionales haluro y alkoxi.
Conclusiones:
- El método desarrollado proporciona una ruta sin precedentes para la resolución quiral de complejos de organomanganeso.
- Este enfoque ofrece una estrategia rentable y versátil para acceder a los compuestos enantiopuros.
- Se prevén amplias aplicaciones en la síntesis de valiosas moléculas quirales, incluidas las ciclohexenonas sustituidas.
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