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Diastereoselectiva Borociclopropanación de éteres alilicos mediante el uso de un carbenoide de borometilzinco

Guillaume Benoit¹, André B Charette¹

¹Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal , P.O. Box 6128, Station Downtown, Montréal, Québec H3C 3J7, Canada.

Journal of the American Chemical Society

|January 19, 2017

Resumen

Un nuevo carbenoide de borometilzinco permite una eficiente borociclopropanación de éteres y estirenos alílicos. Este método produce borociclopropanos 1,2,3 sustituidos altamente diastereoselectivos, bloques de construcción sintéticos versátiles.

Área de la Ciencia:

Química orgánica
Química organometálica

Sus antecedentes:

La ciclopropanación de Simmons-Smith es una reacción orgánica fundamental.
Los compuestos que contienen boro son valiosos intermedios sintéticos.

Objetivo del estudio:

Desarrollar un nuevo método de borociclopropanación.
Para sintetizar los borociclopropanos 1,2,3 sustituidos.
Explorar la utilidad de estos compuestos como bloques de construcción.

Principales métodos:

Preparación de un nuevo precursor de carbenoide de borometilzinco en tres pasos.
Aplicación del carbenoide en la reacción de Simmons-Smith con éteres alilicos y derivados del estireno.
Realización de reacciones de postfuncionalización en los borociclopropanos resultantes.

Principales resultados:

El éxito de la borociclopropanación de éteres y derivados de estireno (E) y (Z).
Se obtienen altos rendimientos y diastereoselectividades en la formación de borociclopropanos 1,2,3 sustituidos.
Demostración de la versatilidad de los borociclopropanos sintetizados a través de reacciones de postfuncionalización.

Conclusiones:

El nuevo carbenoide de borometilzinco proporciona una ruta eficiente hacia los borociclopropanos.
Los borociclopropanos sintetizados son bloques de construcción versátiles para otras transformaciones químicas.

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