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Funcionalización transanular C-H catalizada por el paladio de aminas alicíclicas

Joseph J Topczewski¹, Pablo J Cabrera¹, Noam I Saper¹

¹Department of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, Michigan 48109, United States.

|February 18, 2016

Resumen

Los investigadores desarrollaron un nuevo método para funcionalizar los enlaces C-H en aminas alicíclicas, cruciales para el descubrimiento de fármacos. Esta reacción catalizada por el paladio permite la formación selectiva de enlaces C-C en sitios alejados del nitrógeno, agilizando la síntesis de candidatos farmacéuticos.

Área de la Ciencia:

Química orgánica
Química medicinal
Catálisis

Sus antecedentes:

El descubrimiento farmacéutico requiere sintetizar numerosas moléculas, a menudo utilizando enlaces C-H.
Las aminas alicíclicas son comunes en los productos farmacéuticos, pero son difíciles de funcionalizar remotamente.
Los métodos de funcionalización C-H existentes para estas estructuras son limitados.

Objetivo del estudio:

Desarrollar un método selectivo y eficiente para la funcionalización de C-H en aminas alicíclicas.
Para permitir la formación de enlaces C-C en lugares alejados del átomo de nitrógeno.
Simplificar la síntesis de nuevos candidatos farmacéuticos.

Principales métodos:

Un enfoque transanular que utiliza la conformación de barco de las aminas alicíclicas.
Conversión de enlaces C-H a C-C catalizada por el paladio y dirigida por aminas.
Aplicación en varios andamios de aminas alicíclicas.

Principales resultados:

Se logró una manipulación selectiva de los enlaces C-H en sitios alejados del nitrógeno.
El método demostró su eficacia en diversas estructuras de aminas alicíclicas.
Se sintetizaron nuevos derivados de moléculas bioactivas, incluida la vareniclina.

Conclusiones:

La reacción transanular reportada proporciona una nueva vía para la funcionalización de C-H en aminas alicíclicas.
Este método ofrece una herramienta poderosa para el descubrimiento y desarrollo de fármacos.
Facilita la creación de diversas estructuras moleculares para aplicaciones farmacéuticas.

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