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La reacción de Sila morita-Baylis-Hillman de los ciclopropenos es una reacción de Baylis-Hillman

Stepan Chuprakov¹, Denis A Malyshev, Alexander Trofimov

¹Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois 60607, USA.

Journal of the American Chemical Society

|November 14, 2007

Resumen

Los investigadores demostraron la primera reacción sila-Morita-Bayis-Hillman, un nuevo proceso catalizado por la fosfina. Este método sintetiza de manera eficiente los valiosos 1- ((silyloxymethyl) ciclopropenos utilizando siliciclopropenos y compuestos carbonílicos.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis es la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Los derivados del ciclopropeno son valiosos intermediarios sintéticos.
Los métodos tradicionales para sintetizar ciclopropenos funcionalizados pueden ser limitados.
La reacción Morita-Bayis-Hillman es una conocida reacción de formación de enlaces carbono-carbono.

Objetivo del estudio:

Para desarrollar una nueva reacción sila-Morita-Bayis-Hillman.
Para establecer una nueva ruta sintética para 1- ((silyloxymethyl)cyclopropenes.
Para explorar las transformaciones catalizadas por la fosfina que involucran a los sililciclopropenos.

Principales métodos:

Reacción de los 1-siliciclopropenos con los compuestos carbonílicos.
El uso de catalizadores de fosfina.
Investigando una cascada de reorganización y eliminación de 1,3-Brook.

Principales resultados:

Se logró la primera reacción sila-Morita-Bayis-Hillman exitosa.
Se sintetizó una variedad de 1- ((silyloxymethyl) ciclopropenos.
La reacción procede a través de una cascada de reordenamiento/eliminación de 1,3-Brook.

Conclusiones:

Este trabajo presenta un método novedoso y eficiente para la síntesis de 1- ((silyloxymethyl)cyclopropenes.
La reacción catalizada por fosfina desarrollada ofrece un acceso conveniente a compuestos previamente difíciles de obtener.
Este estudio amplía el alcance de la reacción Morita-Bayis-Hillman a sustratos que contienen silicio.

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