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Ciclopropanación intramolecular de indoles altamente enantioselectiva catalizada por el cobre y el hierro

Huan Xu¹, Yi-Pan Li¹, Yan Cai¹

¹State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University , Tianjin 300071, China.

Journal of the American Chemical Society

|May 27, 2017

Resumen

Los investigadores desarrollaron un nuevo método para crear moléculas complejas a partir de indoles. Este eficiente proceso catalítico produce compuestos policíclicos con un centro estereogénico clave, importante para el descubrimiento de fármacos.

Área de la Ciencia:

Química orgánica
Catálisis
Química medicinal

Sus antecedentes:

Los derivados del indole son andamios cruciales en muchos productos naturales y farmacéuticos.
La síntesis eficiente de compuestos policíclicos con centros estereogénicos cuaternarios sigue siendo un desafío.
La construcción estereoselectiva de la posición 3-indol es vital para la actividad biológica.

Objetivo del estudio:

Desarrollar la primera enantioselectiva ciclopropanación intramolecular de indoles.
Establecer un método sencillo y eficiente para sintetizar compuestos policíclicos complejos a base de indol.
Para crear compuestos con un centro estereogénico cuaternario de carbono en la posición 3-indol.

Principales métodos:

Utilizó complejos de cobre o hierro como catalizadores.
Se emplean espiro bisoxazolinas quirales como ligandos para los catalizadores metálicos.
Se han realizado reacciones de ciclopropanación intramoleculares en sustratos de indol.

Principales resultados:

Logró buenos a altos rendimientos, hasta el 94%.
Se ha demostrado una excelente enantiselectividad, hasta > 99,9% ee.
Se han construido con éxito compuestos policíclicos con un centro estereogénico cuaternario en la posición 3-indol.

Conclusiones:

El método desarrollado es un avance significativo en la funcionalización del indol.
Esta reacción proporciona un acceso eficiente a valiosos derivados policíclicos del indol.
La metodología es prometedora para la síntesis de productos naturales complejos y fármacos candidatos.

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