Reorganizaciones catalíticas enantioselectivas [2,3] de los N-óxidos de aminas

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Hongli Bao¹, Xiangbing Qi, Uttam K Tambar

¹Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States.

Journal of the American Chemical Society

|January 12, 2011

Resumen

Este estudio introduce la primera reorganización enantioselectiva [2,3] catalizada por el paladio de los N-óxidos de aminas alilicas. Este método sintetiza eficientemente alcoholes alelicos quirales no racémicos bajo condiciones suaves.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Síntesis asimétrica de síntesis.

Sus antecedentes:

El reordenamiento de Meisenheimer es una reacción orgánica conocida.
La síntesis enantioselectiva de moléculas complejas sigue siendo un desafío significativo en la química orgánica.

Objetivo del estudio:

Desarrollar una nueva reorganización enantioselectiva [2,3] catalizada por el paladio de los N-óxidos de aminas alilicas.
Establecer un nuevo método para la síntesis de derivados quirales no racémicos alifáticos de alcohol alílico.

Principales métodos:

Reacción catalizada por el paladio de N-óxidos de aminas alilicas.
Técnicas de síntesis enantioselectivas.
Optimización de las condiciones de reacción leve.

Principales resultados:

Se logró la primera reorganización enantioselectiva [2,3] exitosa de N-óxidos de aminas alilicas.
Se sintetizaron derivados de alcohol alelico alifático no racémica quiral con grupos funcionales reactivos.
Se establecieron condiciones de reacción leve, facilitando la síntesis.

Conclusiones:

El método desarrollado representa un reordenamiento asimétrico de Meisenheimer.
Se propone un mecanismo mediado por ciclización para la reacción.
Este trabajo proporciona una nueva herramienta valiosa para la síntesis asimétrica.

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