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Síntesis asimétrica catalítica directa de aminos cíclicos a partir de aldehídos

Xu Cheng¹, Sreekumar Vellalath, Richard Goddard

¹Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1,D-45470, Mülheim an der Ruhr, Germany.

Journal of the American Chemical Society

|November 4, 2008

Resumen

Un nuevo método sintetiza directamente los aminos cíclicos utilizando la catálisis con ácido de Brønsted. Este avance permite la primera síntesis asimétrica de fármacos aminados antihipertensivos como la (R) tiabutazida.

Área de la Ciencia:

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

Sus antecedentes:

Las aminas cíclicas son importantes motivos estructurales en los productos farmacéuticos.
La síntesis directa de aminos cíclicos a menudo carece de enantioselectividad.
La síntesis asimétrica de medicamentos que contienen aminal es un desafío.

Objetivo del estudio:

Desarrollar una síntesis directa altamente enantioselectiva de aminoácidos cíclicos.
Aplicar esta metodología a la síntesis asimétrica de fármacos antihipertensivos.

Principales métodos:

Utilizó una reacción catalizada por ácido de Brønsted.
Los aldehídos empleados como materiales de partida para la formación de aminas cíclicas.
Se logra una síntesis directa con alta enantioselectividad.

Principales resultados:

Se desarrolló con éxito una síntesis directa de aminas cíclicas con alta enantioselectividad.
Demostró la primera síntesis asimétrica de varios fármacos antihipertensivos aminados.
Específicamente sintetizado (R) -Thiabutazide con una alta pureza enantiomérica.

Conclusiones:

El método desarrollado por Brønsted, catalizado por ácido, es eficaz para la síntesis de aminas cíclicas enantioselectivas.
Esta metodología proporciona una ruta valiosa para la síntesis asimétrica de importantes compuestos farmacéuticos.
El enfoque es aplicable a la síntesis de fármacos como el (R) tiabutazido.

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