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Síntesis estereoselectiva multicatalítica de alquenos altamente sustituidos por reacciones de

Ciro Romano¹, Clément Mazet¹

¹Department of Organic Chemistry , University of Geneva , 30 quai Ernest Ansermet , 1211 Geneva , Switzerland.

Journal of the American Chemical Society

|March 22, 2018

Resumen

Este estudio introduce dos nuevas secuencias multicatalíticas para la síntesis estereoselectiva de alquenos altamente sustituidos a partir de éteres alqueno-metilo. Estos métodos combinan eficientemente la isomerización y el acoplamiento cruzado, ofreciendo rutas versátiles a estructuras olefínicas complejas.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La síntesis estereoselectiva de alquenos altamente sustituidos sigue siendo un desafío importante en la química orgánica.
El desarrollo de métodos catalíticos eficientes para la construcción de enlaces complejos C = C es crucial para acceder a nuevas arquitecturas moleculares.

Objetivo del estudio:

Desarrollar dos estrategias complementarias de isomerización/acoplamiento secuencial multicatalítico para la preparación estereoselectiva de alquenos altamente sustituidos.
Explorar la compatibilidad de estos métodos con varios grupos funcionales y patrones de sustitución olefínica.
Establecer variantes enantioselectivas para el acceso a los compuestos olefínicos quirales.

Principales métodos:

Se utilizó un catalizador de iridio catiónico para la isomerización estereoselectiva de éteres metílicos de alilo.
Se utiliza un catalizador de níquel para el posterior acoplamiento de éteres de metilvinilo generados in situ con reactivos de Grignard.
Desarrolló una secuencia catalítica complementaria de paladio/níquel para éteres alquenilmetilo con enlaces C=C remotos.

Principales resultados:

Se ha logrado una síntesis estereoselectiva de alquenos altamente sustituidos con un alto control sobre el enlace C=C recién formado.
Compatibilidad demostrada con grupos funcionales sensibles y diversos patrones de sustitución olefínica.
Se estableció una secuencia [Ir/Ni] altamente enantioselectiva utilizando un precatalizador de iridio quiral.
La secuencia [Pd/Ni] dio alquenos con un estereocontrol más bajo pero permitió la construcción de enlaces C(sp2) -C(sp2) y C(sp2) -C(sp3).

Conclusiones:

Las secuencias multicatalíticas desarrolladas proporcionan rutas eficientes y versátiles a alquenos valiosos y altamente sustituidos.
Estos métodos ofrecen acceso a moléculas complejas que son difíciles de sintetizar utilizando enfoques convencionales.
La capacidad de construir enlaces C(sp2) -C(sp2) y C(sp2) -C(sp3) expande la utilidad sintética de estos sistemas catalíticos.

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