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Síntesis asimétrica catalítica de las aziridinas trisubstituidas

Li Huang¹, William D Wulff

¹Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.

Journal of the American Chemical Society

|May 24, 2011

Resumen

Este estudio introduce una síntesis catalítica asimétrica directa para las aziridinas trisubstituidas utilizando iminas N-Boc y compuestos diazo específicos. El método logra una alta diastereoselectividad y enantioselectividad, avanzando la química orgánica sintética.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Síntesis asimétrica de síntesis.

Sus antecedentes:

Las aziridinas trisubstituidas son valiosos intermediarios sintéticos.
La síntesis catalítica asimétrica directa de estos compuestos sigue siendo un desafío.
Los métodos anteriores mostraron una reactividad limitada con las iminas no activadas.

Objetivo del estudio:

Desarrollar un método catalítico asimétrico directo para la síntesis de aziridinas trisubstituidas.
Para explorar la reactividad de las iminas N-Boc con los compuestos α-diazocarbonilo.
Para lograr un alto control estereoquímico en la formación de aziridina.

Principales métodos:

Empleando un enfoque catalítico asimétrico directo.
Utilizando las iminas N-Boc como sustratos.
Reaccionan las iminas N-Boc con los ésteres α-diazo y las α-diazo-N-aciloxazolidinonas.

Principales resultados:

Síntesis exitosa de aziridinas trisubstituidas de las iminas N-Boc.
Se ha demostrado una alta diastereoselectividad y enantioselectividad.
Superó las limitaciones de la reactividad de las iminas no activadas.

Conclusiones:

El método desarrollado proporciona un acceso eficiente a las aziridinas quirales trisubstituidas.
Las iminas N-Boc son sustratos adecuados para esta transformación catalítica.
Este trabajo amplía el alcance de la síntesis asimétrica de aziridina.

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