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La hidrogenación asimétrica catalizada por iridio-monodentato-fosforamidita de las iminas N-H de la benzofenona

Guohua Hou¹, Ran Tao, Yongkui Sun

¹Department of Chemistry, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854-8066, USA.

Journal of the American Chemical Society

|January 29, 2010

Resumen

Este estudio presenta un nuevo método para crear aminas quirales utilizando hidrogenación asimétrica homogénea. El proceso produce de manera eficiente valiosas aminas quirales a partir de iminas de benzofenona sin protección con una alta enantioselectividad.

Área de la Ciencia:

Química orgánica es la química orgánica.
Catalización asimétrica por catálisis asimétrica.
Química verde es la química verde.

Sus antecedentes:

Las aminas quirales son bloques de construcción cruciales en productos farmacéuticos y productos químicos finos.
El desarrollo de sistemas catalíticos eficientes para la hidrogenación asimétrica sigue siendo un desafío clave.

Objetivo del estudio:

Desarrollar un nuevo método de hidrogenación asimétrico homogéneo para las iminas N-H de la benzofenona sin protección.
Para lograr altos rendimientos y enantioselectividades para la síntesis de aminas quirales.

Principales métodos:

Se utilizó un catalizador basado en iridio, específicamente Ir-(S) -N-benzil-N-metil-monofos.
Se realizó una hidrogenación asimétrica homogénea en una gama de iminas N-H de la benzofenona sin protección (1a-r).

Principales resultados:

Se obtuvieron altos rendimientos (80-96%) para las aminas quirales objetivo (2a-r).
Se obtienen excelentes enantioselectividades, hasta el 98% ee, especialmente para sustratos orto-sustituidos.
Demostró con éxito el método en 18 ejemplos diversos.

Conclusiones:

La hidrogenación ir catalizada desarrollada es un método eficaz para sintetizar aminas quirales.
El protocolo demuestra una amplia aplicabilidad y alta eficiencia, especialmente para sustratos estéricamente obstaculizados.

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