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Un nuevo método sintético para la sal de alfa-alcoxicarbonilo ininio y su reacción con los nucleófilos

Makoto Shimizu¹, Hiroyuki Itou, Megumi Miura

¹Department of Chemistry for Materials, Mie University, Tsu, Mie 514-8507, Japan. mshimizu@chem.mie-u.ac.jp

Journal of the American Chemical Society

|March 10, 2005

Resumen

Los investigadores sintetizaron fácilmente sales de iminio a partir de aminoceteno silil acetalo a través de la oxidación. La adición nucleofílica posterior a estas sales de iminio produjo eficientemente valiosos ésteres alfa-amino.

Área de la Ciencia:

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

Sus antecedentes:

Los ésteres alfa-amino son bloques de construcción cruciales en los productos farmacéuticos y productos naturales.
La síntesis eficiente de alfa-amino ésteres sigue siendo un área activa de investigación.

Objetivo del estudio:

Desarrollar un método sencillo para la síntesis de alfa-amino ésteres.
Para explorar la utilidad de las sales de iminio derivadas de aminoceteno silyl acetals.

Principales métodos:

Oxidación de los acetales silílicos de aminoceteno mediante el uso de 2,3-dicloro-5,6-dician-1,4-benzoquinona (DDQ).
Adición nucleofílica al intermediario de sal de iminio generado in situ.

Principales resultados:

Las sales de iminio se preparaban fácilmente en condiciones suaves.
La adición nucleofílica procedió de manera eficiente, produciendo ésteres alfa-amino.
Se obtuvieron buenos rendimientos de los productos deseados.

Conclusiones:

Este estudio presenta una ruta fácil y eficiente a los alfa-amino ésteres.
El método utiliza materiales de partida y reactivos fácilmente accesibles.
Las sales de iminio generadas son versátiles intermediarios para la formación de enlaces C-C.

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