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Hidrogenación enantioselectiva de las iminas N-H

Guohua Hou¹, Francis Gosselin, Wei Li

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

|July 3, 2009

Resumen

Los investigadores desarrollaron un método sencillo para sintetizar las cetoiminas N-H. La hidrogenación asimétrica de estos compuestos utilizando un catalizador de iridio produce valiosas aminas quirales con alta eficiencia y enantioselectividad.

Área de la Ciencia:

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

Sus antecedentes:

Las cetoiminas N-H son versátiles intermediarios sintéticos.
La síntesis eficiente y la transformación de las cetoiminas N-H son cruciales para acceder a las aminas quirales.

Objetivo del estudio:

Desarrollar una preparación de alto rendimiento de cetoiminas N-H.
Para lograr una hidrogenación asimétrica eficiente de las cetoiminas N-H para producir aminas quirales.

Principales métodos:

Adición organometálica a los nitriles para la síntesis de N-H cetoimina.
Hidrogenación asimétrica homogénea utilizando el catalizador de Ir-(S,S) -f-binafano.

Principales resultados:

Las cetoiminas N-H (3a-3v) fueron sintetizadas en alto rendimiento como sales estables de clorhidrato.
Las aminas quirales (4a-4v) se obtuvieron en un rendimiento del 90-95% con una enantioselectividad de hasta el 95%.

Conclusiones:

Se ha establecido una ruta sintética robusta para las cetoiminas N-H y su posterior hidrogenación asimétrica.
Este método proporciona acceso a valiosas aminas quirales con un excelente control estéreo.

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