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Síntesis enantioselectiva de anillos de tamaño medio anulados por indoles

Lin Huang¹, Li-Xin Dai¹, Shu-Li You^1,2

¹State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.

Journal of the American Chemical Society

|April 20, 2016

Resumen

Este estudio presenta un nuevo método catalizado por iridio para crear compuestos complejos de indol. La eficiente reacción en cascada produce valiosos anillos de tamaño medio con alta precisión.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los compuestos de anillo de tamaño mediano son importantes en la química medicinal, pero son difíciles de sintetizar.
La síntesis asimétrica es crucial para el desarrollo de productos farmacéuticos enantioméricamente puros.
Las reacciones en cascada ofrecen vías eficientes a arquitecturas moleculares complejas.

Objetivo del estudio:

Desarrollar una nueva síntesis asimétrica para anillos de tamaño medio anulados por indol.
Para establecer una reacción en cascada catalizada por iridio para una eficiente formación de anillos.
Explorar el alcance y las limitaciones del método sintético desarrollado.

Principales métodos:

Reacción en cascada de desaromatización/retro-Mannich/hidrólisis alilica catalizada por iridio.
Optimización de las condiciones de reacción que incluyen catalizador, ligando, disolvente y temperatura.
Reducción in situ para estudios mecanicistas y captura intermedia.

Principales resultados:

Síntesis exitosa de compuestos anulados por indol de siete, ocho y nueve miembros.
Se obtienen rendimientos de buenos a excelentes y una excelente enantioselectividad para los compuestos objetivo.
Demostró un amplio alcance de sustrato para la reacción en cascada desarrollada.

Conclusiones:

La reacción en cascada catalizada por iridio desarrollada proporciona una ruta eficiente y enantioselectiva a los complejos anillos de tamaño medio anulados por indol.
Las condiciones de reacción suaves y el amplio alcance del sustrato hacen que esta metodología sea ampliamente aplicable.
Las investigaciones mecanicistas apoyan la vía de reacción propuesta que implica un intermediario desaromatizado.

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