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Bromoclorinación catalítica quimio, regio y enantioselectiva de los alcoholes alelicos por medio de la

Dennis X Hu¹, Frederick J Seidl¹, Cyril Bucher¹

¹Department of Chemistry, Stanford University, Stanford, California 94305, United States.

Journal of the American Chemical Society

|March 5, 2015

Resumen

Este estudio introduce una nueva bromocloración enantioselectiva de los alcoholes alílicos utilizando un catalizador de base de Schiff. Este método permite la síntesis eficiente de moléculas complejas bromocloradas y compuestos relacionados.

Área de la Ciencia:

Química orgánica es la química orgánica.
Catalización asimétrica por catálisis asimétrica.

Sus antecedentes:

Los alcoholes aliales son versátiles intermediarios sintéticos.
Los métodos eficientes para la halogenación enantioselectiva son cruciales en la síntesis orgánica.

Objetivo del estudio:

Desarrollar una bromoclorinación altamente quimio, regio y enantioselectiva de los alcoholes alílicos.
Para utilizar fuentes de halógenos fácilmente disponibles y un simple catalizador quiral de base Schiff.

Principales métodos:

Reacción de los alcoholes alílicos con la N-bromosuccinimida y la N-clorosuccinimida.
Empleando un catalizador quiral de base de Schiff para la inducción enantioselectiva.
Exploración del alcance del sustrato y síntesis de un producto natural.

Principales resultados:

Se obtienen altos rendimientos y una excelente enantioselectividad en la bromocloración.
Demostró la aplicabilidad de la reacción a diversos sustratos de alcohol alílico.
Con éxito sintetizó un producto natural bromoclorado enantioselectivamente.

Conclusiones:

La reacción catalizada por bases de Schiff desarrollada ofrece una ruta eficiente a los compuestos bromoclorados enriquecidos enantioméricamente.
La metodología es versátil y puede extenderse a las reacciones de dibrominación y diclorinación relacionadas.

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