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Oro ((I) -Síntesis estereoselectiva directa catalizada de desoxiglicosidos a partir de glicalos

Carlos Palo-Nieto¹, Abhijit Sau¹, M Carmen Galan¹

¹School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.

Journal of the American Chemical Society

|September 23, 2017

Resumen

El oro (I) y el triflato de plata catalizan una nueva síntesis directa de desoxiglicosidos a partir de glicalos. Esta reacción eficiente procede a través de la hidrofuncionalización catalizada por oro, que ofrece un método versátil para crear carbohidratos complejos.

Área de la Ciencia:

Química orgánica
Catálisis
Química de los carbohidratos

Sus antecedentes:

Los desoxiglicosidos son componentes cruciales en las moléculas biológicamente activas.
Los métodos sintéticos existentes para los desoxiglicosidos a menudo carecen de estereoselectividad o requieren condiciones duras.
Es muy deseable el desarrollo de métodos catalíticos eficientes y estereoselectivos.

Objetivo del estudio:

Desarrollar una nueva síntesis catalítica directa y α-estereoselectiva de desoxiglicosidos.
Explorar la utilidad de la catálisis del oro en la síntesis de carbohidratos.
Para aclarar el mecanismo de reacción para esta transformación.

Principales métodos:

Se utilizan catalizadores de oro en combinación con triflato de plata (AgOTf).
Se emplean glicalos como materiales de partida y varios nucleófilos hidroxilo.
Estudios mecanicistas realizados, incluida la identificación intermedia y el análisis cinético.

Principales resultados:

Se logró una síntesis catalítica directa y α-estereoselectiva sin precedentes de desoxiglicosidos a partir de glicosidos.
La reacción procede eficientemente a temperatura ambiente con altos rendimientos.
Se ha demostrado un amplio alcance del sustrato, alojando diversos donantes glicosílicos y nucleófilos hidroxilo.

Conclusiones:

El sistema gold ((I) /AgOTf desarrollado proporciona un método potente y versátil para la síntesis de desoxiglicosidos.
El mecanismo de reacción implica la hidrofuncionalización catalizada por Au (I) de la fracción de éter enol de los glicosilos.
Esta metodología ofrece un avance significativo en la síntesis catalítica de carbohidratos.

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