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La aminohidroxilación catalizada por el hierro de las olefinas
Kevin S Williamson1, Tehshik P Yoon
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
Journal of the American Chemical Society
|March 18, 2010
Resumen
Las sales de hierro catalizan las reacciones de las N-sulfoniloxaziridinas con las olefinas, produciendo 1,3-oxazolidinas. Esto proporciona una nueva ruta a los 1,2-aminoalcoholes con regioselectividad controlable utilizando catalizadores metálicos de bajo costo.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Metodología sintética de la metodología sintética.
Sus antecedentes:
- El acceso a los 1,2-aminoalcoholes es crucial en la síntesis orgánica.
- Los métodos anteriores, como la oxiaaminación catalizada por cobre, ofrecían un limitado control de regioselectividad.
- El desarrollo de sistemas catalíticos alternativos es necesario para diversas aplicaciones sintéticas.
Objetivo del estudio:
- Para descubrir un nuevo sistema catalítico para la síntesis de 1,3-oxazolidinas.
- Desarrollar un nuevo método para sintetizar 1,2-aminoalcoholes con regioselectividad sintonizable.
- Explorar el uso de metales de transición baratos de primera fila como catalizadores.
Principales métodos:
- Reacción de las N-sulfoniloxaziridinas con varias olefinas.
- Catálisis utilizando sales de hierro.
- Análisis de los productos de reacción, incluidas las 1,3-oxazolidinas y los subsiguientes 1,2-aminoalcoholes.
Principales resultados:
- Las N-sulfoniloxaziridinas reaccionan con una amplia gama de olefinas en presencia de sales de hierro para producir 1,3-oxazolidinas.
- Este proceso catalizado por hierro proporciona 1,2-aminoalcoholes con regioselectividad opuesta a los métodos catalizados por cobre.
- La elección de un catalizador de metales de transición de primera fila, barato y no tóxico, permite controlar el sentido de regioselectividad.
Conclusiones:
- Se ha desarrollado una nueva síntesis regioselectiva de 1,2-aminoalcoholes utilizando la catálisis del hierro.
- Este método ofrece una regioselectividad complementaria a las rutas catalizadas por cobre existentes.
- La capacidad de controlar la regioselectividad a través de la elección del catalizador mejora la flexibilidad sintética.
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