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Síntesis de enonas C6 y C7 enantiopuro altamente sustituidas
Jerry Evarts1, Eduardo Torres, Philip L Fuchs
1Contribution from the Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Journal of the American Chemical Society
|September 13, 2002
Resumen
Las sulfonas de epoxivinilo enantiopuro se sintetizan y sirven como bloques de construcción quirales. Estos compuestos permiten la síntesis estereospecífica de cicloalquenonas sustituidas, ofreciendo una ruta versátil para la construcción de moléculas complejas.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Síntesis asimétrica de síntesis.
Sus antecedentes:
- Las sulfonas de epoxivinilo son valiosos intermediarios sintéticos.
- Los bloques de construcción quirales son esenciales para la síntesis enantioselectiva.
Objetivo del estudio:
- Para desarrollar enantiopuro epoxyvinyl sulfones (SS-9a, SS-9b) mediante el uso de la epoxidación de Jacobsen.
- Para utilizar estos compuestos como plantillas para la construcción de cicloalquenonas sustituidas.
- Para explorar su utilidad como equivalentes sintéticos quirales de las enonas.
Principales métodos:
- Epoxidación de Jacobsen de 2-fenilsulfonil 1,3-ciclohexa y cicloheptadieno.
- Adición estereospecífica de nucleófilos de carbono a las sulfonas de epoxivinilo.
- Construcción de las enantiopuras alfa, beta y gamma sustituidas por cicloalquenonas.
Principales resultados:
- Adición estereospecífica y de alto rendimiento de nucleófilos de carbono a SS-9a y SS-9b.
- Construcción eficiente de las cicloalquenonas sustituidas por enantiopuro.
- Demostración de las sulfonas de epoxivinilo como versátiles síntonas quirales.
Conclusiones:
- Las sulfonas de epoxivinilo enantiopuro son fácilmente accesibles a través de la epoxidación de Jacobsen.
- Estas sulfonas son plantillas quirales efectivas para la síntesis de cicloalquenonas complejas.
- La metodología proporciona una poderosa herramienta para la síntesis asimétrica de enonas cíclicas.
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