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Arilaciones enantioselectivas deshidrogenativas de tres alquenos sustituidos con indoles para construir

Chun Zhang¹, Celine B Santiago¹, Jennifer M Crawford¹

¹Department of Chemistry, University of Utah , Salt Lake City, Utah 84112, United States.

Journal of the American Chemical Society

|December 2, 2015

Resumen

Se ha desarrollado un nuevo método para crear moléculas complejas con estereocentros cuaternarios remotos. Esta arilación enantioselectiva de Heck utiliza un nuevo ligando quiral para lograr una alta selectividad en la síntesis de valiosos derivados de indol.

Área de la Ciencia:

Química orgánica
Catálisis asimétrica

Sus antecedentes:

Los estereocentros cuaternarios son motivos estructurales cruciales en muchos productos farmacéuticos y naturales.
El desarrollo de métodos eficientes para su síntesis asimétrica sigue siendo un desafío importante en la química orgánica.

Objetivo del estudio:

Desarrollar una reacción de arilación de Heck enantioselectiva y deshidrogenativa intermolecular.
Construir estereocentros cuaternarios remotos utilizando alquenos tres sustituidos y derivados de indol.

Principales métodos:

Utilizó un nuevo ligando quiral de piridina oxazolina para la catálisis.
Investigó el alcance de la reacción con varios derivados de indol y alquenos trisubstituidos.

Principales resultados:

Se ha logrado una enantioselectividad de buena a alta para varias combinaciones de sustratos.
Se han identificado variaciones en la enantioselectividad dependientes del sustrato.

Conclusiones:

El método desarrollado ofrece una nueva vía para los compuestos enriquecidos enantioméricamente con estereocentros cuaternarios.
Las correlaciones estructura-enantioselectividad se utilizaron para guiar el diseño de ligandos mejorados para estudios futuros.

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