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Reducción concisa de las aminas secundarias y terciarias con un núcleo de tetrahidroisoquinolina a través de un

Yue Ji¹, Lei Shi^1,2, Mu-Wang Chen¹

¹State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, P. R. China.

Journal of the American Chemical Society

|August 15, 2015

Resumen

Este estudio presenta un método simplificado para crear aminas quirales a partir de mezclas racémicas. Un nuevo proceso de un solo recipiente produce eficientemente tetrahidroisoquinolinas enriquecidas enantioméricamente con alta pureza y rendimiento.

Área de la Ciencia:

Química orgánica
Síntesis asimétrica
Catálisis

Sus antecedentes:

Las aminas quirales son bloques de construcción cruciales en productos farmacéuticos y productos químicos finos.
Los métodos existentes para la síntesis de aminas quirales pueden ser complejos y de varios pasos.

Objetivo del estudio:

Desarrollar un método directo y eficiente de desacimización de aminas secundarias y terciarias.
Establecer una vía sintética escalable para las 1,2,3,4-tetrahidroisoquinolinas quirales sustituidas.

Principales métodos:

Un proceso redox de un solo recipiente que combina la oxidación de N-bromosuccinimida y la hidrogenación asimétrica catalizada por iridio.
Utilizando un núcleo de tetrahidroisoquinolina para la desacemiación.

Principales resultados:

Se ha conseguido la desacimización de las aminas racémicas secundarias y terciarias.
Se generan 1,2,3,4-tetrahidroisoquinolinas quirales sustituidas con un exceso enantiomérico de hasta el 98%.
Se obtienen altos rendimientos de hasta el 93%.

Conclusiones:

El método desarrollado ofrece una técnica simple, escalable y eficiente para sintetizar aminas quirales.
Este enfoque proporciona acceso directo a las tetrahidroisoquinolinas enriquecidas enantioméricamente a partir de materiales de partida racémicos.

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