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Protodeboronation de ésteres borónicos terciarios: síntesis asimétrica de centros estereogénicos de alquilo

Stefan Nave¹, Ravindra P Sonawane, Tim G Elford

¹School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.

Journal of the American Chemical Society

|November 18, 2010

Resumen

Los ésteres borónicos terciarios ahora pueden ser protodeboronados de manera eficiente utilizando fluoruro de cesio o fluoruro de tetrabutylammonio trihidrato. Este método conserva la configuración estereoquímica y permite el etiquetado con deuterio de los alcanos quirales.

Área de la Ciencia:

Química orgánica es la química orgánica.
Metodología sintética de la metodología sintética.
Síntesis estereoselectiva de síntesis.

Sus antecedentes:

Los boranos terciarios son fácilmente protodeborados por los ácidos carboxílicos.
Los ésteres borónicos terciarios carecen de un método de protodeboronización eficiente.
El desarrollo de nuevas rutas sintéticas es crucial para acceder a moléculas complejas.

Objetivo del estudio:

Desarrollar un método de protodeboronización eficiente para los ésteres borónicos terciarios.
Para lograr la protodeboronización estereorretentiva de los ésteres borónicos quirales terciarios.
Para permitir la síntesis de alcanes quirales etiquetados con deuterio.

Principales métodos:

Protodeboronation de ésteres borónicos terciarios utilizando fluoruro de cesio (CsF) y agua.
Protodeboronation utilizando el fluoruro de tetrabutylammonio y el trihidrato (TBAF·3H2O).
Utilizando óxido de deuterio (D2O) para el etiquetado de deuterio.

Principales resultados:

Se logró una protodeboronización altamente eficiente de ésteres borónicos terciarios.
Retención esencial y completa de la configuración observada durante la protodeboronación.
Síntesis exitosa de alcanes terciarios enantioenriquecidos etiquetados con deuterio.
Aplicación para la síntesis de (S) -turmerona.

Conclusiones:

Desarrolló un método novedoso, eficiente y estereoretativo de protodeboronation para los ésteres borónicos terciarios.
El método proporciona acceso a valiosos alcanos quirales etiquetados con deuterio.
Demostró la utilidad de esta metodología en la síntesis de productos naturales.

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