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Un método general y modular para la síntesis asimétrica catalítica de ésteres de alquilboronato

Jens Schmidt¹, Junwon Choi¹, Albert Tianxiang Liu¹

¹Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.

Science (New York, N.Y.)

|December 13, 2016

Resumen

Los investigadores desarrollaron un nuevo método utilizando un catalizador quiral de níquel para acoplamientos alquilo-alquilo estereoconvergentes. Esto proporciona acceso a valiosos ésteres de alquilboronato enriquecidos con enantio para la ciencia farmacéutica y la síntesis de la química orgánica.

Área de la Ciencia:

Química orgánica
Catálisis
Química sintética

Sus antecedentes:

Los compuestos de alquilborón son intermedios cruciales en la ciencia farmacéutica y la química orgánica.
La síntesis estereoquímica controlada de ésteres de alquilboronato enriquecidos con enantio es muy valiosa.
Las transformaciones de los enlaces carbono-boro permiten diversas aplicaciones sintéticas.

Objetivo del estudio:

Desarrollar un nuevo método para sintetizar ésteres de alquilboronato enriquecidos con enantio.
Obtener acoplamientos alquilo-alquilo estereoconvergentes utilizando materiales de partida fácilmente disponibles.
Demostrar la utilidad de los compuestos sintetizados en otras transformaciones sintéticas.

Principales métodos:

Utilizó un catalizador quiral de níquel para la reacción de acoplamiento.
Se utilizan como sustratos α-haloboronatos y reactivos organozinc.
Reacciones realizadas en condiciones suaves.

Principales resultados:

Se ha logrado el acoplamiento estereoconvergente de enlaces alquilo-alquilo.
Generó una amplia gama de ésteres de alquilboronato enriquecidos con enantio.
Se ha demostrado el acceso directo a moléculas quirales que contienen boro.

Conclusiones:

El método desarrollado catalizado por níquel ofrece una vía eficiente para obtener ésteres de alquilboronato enantioenriquecidos.
Estos compuestos quirales de boro son bloques de construcción versátiles en la síntesis orgánica.
La metodología facilita el acceso a productos intermedios valiosos para el descubrimiento y desarrollo de fármacos.

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