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Acoplamientos estereoselectivos en tándem bis-electrófilos de diborilmetano

Stephanie A Murray¹, Michael Z Liang¹, Simon J Meek¹

¹Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.

Journal of the American Chemical Society

|September 23, 2017

Resumen

Una nueva reacción de acoplamiento catalizada por cobre une eficientemente los epóxidos y los electrofilos de alelo. Este método crea valiosos compuestos de organoboron C ((sp3), útiles para sintetizar moléculas complejas como los polioles 1,3.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

El desarrollo de métodos eficientes para la formación de enlaces carbono-carbono es crucial en la síntesis orgánica.
La síntesis estereoselectiva de moléculas orgánicas complejas, como los polioles, sigue siendo un desafío significativo.

Objetivo del estudio:

Para revelar una nueva reacción de acoplamiento de tres componentes catalizada por cobre.
Para permitir la formación estereoselectiva de dos enlaces C-C en un solo centro de carbono.

Principales métodos:

Utilizando un catalizador de cobre para la reacción.
Utilizando el [B(pin) ]2-metano como reactivo conjuntivo.
Acoplamiento de epóxidos y electrofiles de alelo.

Principales resultados:

Se ha logrado la formación de grupos funcionales de organoboron C ((sp3).
Se obtienen productos de alto rendimiento (42-99%) con una excelente diastereoselectividad (>20:1 dr).
Utilidad demostrada en alilación estereospecífica, acoplamiento cruzado en tándem y síntesis de 1,3-poliol.

Conclusiones:

El método de acoplamiento desarrollado ofrece un enfoque potente y estereoselectivo para la construcción de arquitecturas moleculares complejas.
Esta metodología proporciona acceso a valiosos intermediarios de organoboron C ((sp3) y diversas estructuras orgánicas.

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