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Espirocetalización enantio y diastereoselectiva catalizada por el complejo de iridio quiral

James Y Hamilton¹, Simon L Rössler¹, Erick M Carreira¹

¹Eidgenössische Technische Hochschule Zürich , Vladimir-Prelog-Weg 3, HCI H335, 8093 Zürich, Switzerland.

Journal of the American Chemical Society

|June 10, 2017

Resumen

La catálisis del complejo de iridio permite una síntesis eficiente de espiroketales complejos a partir de carbonatos alílicos. Este método instala múltiples estereocentros en un solo paso, ofreciendo una amplia aplicabilidad para diversas estructuras.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Los espiroketales son motivos estructurales importantes en los productos naturales y farmacéuticos.
Los métodos eficientes para la construcción de espiroketas complejos con alto estereocontrol son muy buscados.

Objetivo del estudio:

Desarrollar un nuevo método catalizado por iridio para la síntesis enantio y diastereoselectiva de espiroketales sustituidos.
Para permitir la instalación de múltiples centros estereogénicos en una sola operación sintética.

Principales métodos:

Utilizó un complejo de iridio-P,olefina como catalizador.
Se emplean carbonatos alilicos racémicos como materiales de partida.
Reacciones en cascada investigadas que acoplan la espiroketalización a procesos reversibles.

Principales resultados:

Se ha logrado una formación altamente enantio- y diastereoselectiva de espirocetos sustituidos.
Eficacia demostrada para varios tamaños de anillos, sustituyentes y heteroátomos.
Se ha acoplado con éxito la transformación con procesos reversibles para un control estéreo adicional.

Conclusiones:

El protocolo desarrollado proporciona una poderosa estrategia para la construcción de espiroketas complejos con un preciso control estereoquímico.
Este método ofrece una plataforma versátil para acceder a diversos andamios espiroketales con aplicaciones potenciales en química medicinal.

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