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La aminoacetoxilación de alquenos catalizada por el paladio que forma anillos
Erik J Alexanian1, Chulbom Lee, Erik J Sorensen
1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
Journal of the American Chemical Society
|May 26, 2005
Resumen
Una nueva reacción catalizada por el paladio forma heterociclos que contienen nitrógeno a partir de alquenos. Esta aminoacetoxilación estereoselectiva ofrece una valiosa alternativa a los métodos existentes para la difuncionalización de alquenos.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Metodología sintética de la metodología sintética.
Sus antecedentes:
- El desarrollo de métodos eficientes para sintetizar heterociclos que contienen nitrógeno es crucial en la química medicinal y la ciencia de los materiales.
- Las reacciones de difuncionalización de alquenos catalizados por metales existentes a menudo exhiben estereoselectividad limitada o requieren condiciones duras.
Objetivo del estudio:
- Desarrollar un método suave y eficiente catalizado con paladio para la alqueno aminoacetoxilación.
- Para sintetizar diversos heterociclos que contienen nitrógeno.
- Para investigar los resultados regionales y estereocímicos de la reacción.
Principales métodos:
- Reacción catalizada por paládio (II) de alquenos con varios nucleófilos de nitrógeno.
- Utilizado PhI(OAc) 2 como un oxidante de yodo hipervalente.
- Los productos de reacción analizados utilizando técnicas espectroscópicas estándar.
Principales resultados:
- Se logró con éxito una ligera aminoacetoxilación formadora de anillos catalizada por el paladio (II) de alquenos.
- Sintetizó una variedad de heterociclos que contienen nitrógeno.
- Se han demostrado altos niveles de región de reacción y estereocontrol, procedendo a través de una vía estereoselectiva de difuncionalización de transalquenos.
Conclusiones:
- La aminoacetoxilación desarrollada es un método versátil y eficaz para la construcción de heterociclos de nitrógeno.
- Esta reacción ofrece una valiosa alternativa de transdifuncionalización estereoselectiva a los métodos cis-selectivos existentes.
- La metodología es prometedora para la síntesis simplificada de moléculas complejas que contienen nitrógeno.
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