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Diaminación vicinal de alquenos bajo catálisis Rh

David E Olson¹, Justin Y Su, D Allen Roberts

¹Department of Chemistry, Stanford University , Stanford, California 94305-5080, United States.

Journal of the American Chemical Society

|September 19, 2014

Resumen

Una nueva reacción en tándem crea diaminas protegidas de la aziridinación y el reordenamiento. Este método eficiente sintetiza valiosas diaminas vecinas, incluidas las que se encuentran en la enduracididina.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.

Sus antecedentes:

Las 1,2-diaminas son bloques de construcción cruciales en la síntesis orgánica.
Los métodos existentes para sintetizar 1,2-diaminas pueden ser largos o requerir condiciones duras.

Objetivo del estudio:

Desarrollar un método novedoso y eficiente de un solo paso para sintetizar diaminas vicinales diferencialmente protegidas.
Para demostrar la utilidad de este nuevo método en la síntesis de productos naturales complejos.

Principales métodos:

Una secuencia en tándem que involucra aziridinación catalizada por Rh seguida de una reorganización promovida por NaI.
Apertura del anillo de los intermediarios de sulfamida cíclica en agua caliente y piridina.

Principales resultados:

Síntesis exitosa de 1,2-diaminas a través de un proceso en tándem de un solo paso.
Generación de diaminas vicinales protegidas diferencialmente a través de la apertura fácil del anillo.
Aplicación del método para sintetizar (±) -enduracididina y (±) -alo-enduracididina.

Conclusiones:

La reacción en tándem desarrollada ofrece una ruta eficiente a valiosos derivados de 1,2-diamina.
Esta metodología proporciona una plataforma versátil para acceder a moléculas complejas, incluidos los productos naturales.

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