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Síntesis asimétrica de borilacanos a través de la hidroalición enantioselectiva catalizada por cobre

Jung Tae Han¹, Won Jun Jang¹, Namhyeon Kim¹

¹Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.

Journal of the American Chemical Society

|November 4, 2016

Resumen

Los investigadores desarrollaron un nuevo método catalizado por cobre para sintetizar borilacanos secundarios quirales. Este proceso eficiente utiliza fosfatos y hidrosilanos alilicos, produciendo compuestos valiosos con alta enantioselectividad para aplicaciones potenciales.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los borilacanos secundarios quirales son intermediarios sintéticos muy versátiles.
El desarrollo de métodos enantioselectivos eficientes para su síntesis sigue siendo un desafío.

Objetivo del estudio:

Establecer una hidroalición regioselectiva y enantioselectiva catalizada por cobre para la preparación de borilacanos secundarios enriquecidos con enantio.
Demostrar la utilidad de los borilacanos sintetizados en otras aplicaciones sintéticas.

Principales métodos:

Hidroalilación catalizada por el cobre de los boronatos de alquenilo y las boramidas utilizando hidrosilanos y fosfatos alelicos.
Empleando un ligando quiral de Walphos junto con un catalizador de cobre.
Utilizando una gama de compuestos de alquenilborón con diversos sustituyentes (arilo, heteroarilo, alquilo).

Principales resultados:

Se ha logrado una síntesis eficiente de compuestos de alquilborón homoalílicos secundarios.
Se obtienen buenos rendimientos y altas enantioselectividades (hasta el 99% ee).
Se ha demostrado la aplicación exitosa de los alquilboronatos sintetizados en la síntesis de (S) -massoialactona.

Conclusiones:

El método desarrollado proporciona una ruta eficiente a los borilacanos secundarios enriquecidos con enantio.
La metodología ofrece un amplio alcance de sustrato y un alto control estéreo.
Los borilacanos sintetizados son bloques de construcción valiosos para la síntesis de moléculas complejas.

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