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Funcionalización alilica estereospecífica: las reacciones de los complejos de alilboronato con electrófilos

Cristina García-Ruiz1, Jack L-Y Chen1, Christopher Sandford1

  • 1School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.

Journal of the American Chemical Society
|October 14, 2017
PubMed
Resumen

Los complejos de alilboronato, activados por el arilitio, muestran una gran reactividad hacia diversos electrófilos. Este avance permite la síntesis eficiente de moléculas complejas con nuevas funcionalidades y estereocentros.

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Área de la Ciencia:

  • Química organometálica
  • Química orgánica sintética

Sus antecedentes:

  • Los ésteres alilborónicos son nucleófilos conocidos, que reaccionan principalmente con los carbonilos y las iminas.
  • Su reactividad está limitada a una gama más amplia de especies electrófilas.

Objetivo del estudio:

  • Para mejorar la nucleofilicidad de los ésteres alilborónicos.
  • Para ampliar el alcance de los electrófilos que reaccionan con los reactivos de alliboro.
  • Desarrollar un nuevo método para sintetizar moléculas funcionales con alto control estéreo.

Principales métodos:

  • Activación de ésteres alilborónicos mediante el uso de reactivos de arillitio para formar complejos de alilboronato.
  • Reacción de los complejos activados con varios electrófilos, incluidos el trofilio, el benzoditiolilio, las piridinas activadas, la sal de Eschenmoser, el reactivo de Togni, Selectfluor, el diisopropil azodicarboxilato (DIAD) y MeSX.
  • Análisis de los productos de reacción para los resultados regio- y estereoquímicos.

Principales resultados:

  • Los complejos de alilboronato exhibieron una nucleofilia significativamente mejorada, de 7 a 10 órdenes de magnitud mayor que los ésteres borónicos de origen.
  • La adición exitosa a una amplia gama de electrófilos se logró con un alto control regional y estéreo.
  • El protocolo proporciona acceso a nuevas funcionalidades, incluidos los centros estereogénicos cuaternarios con grupos de flúor y trifluorometil.

Conclusiones:

  • La activación mediada por arillitio aumenta dramáticamente la reactividad de los ésteres alilborónicos.
  • Este método ofrece un enfoque versátil y potente para la síntesis estereoselectiva de moléculas orgánicas complejas.
  • El protocolo desarrollado amplía la utilidad sintética de los reactivos de alilborón en la química orgánica.