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Síntesis asimétrica de alcoholes sintéticos y anti-1,3 aminoácidos

Takuya Kochi¹, Tony P Tang, Jonathan A Ellman

¹Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.

Journal of the American Chemical Society

|June 6, 2002

Resumen

Los investigadores desarrollaron un nuevo método utilizando metalloenaminas de N-sulfinil iminas para la adición diastereoselectiva a los aldehídos. Esto proporciona una ruta versátil para sintetizar valiosos derivados de alcohol sintético y anti-1,3-amino con alta pureza.

Área de la Ciencia:

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

Sus antecedentes:

Las metaloenaminas son versátiles intermediarios sintéticos.
Las iminas de N-sulfinilo ofrecen control estereoquímico en las reacciones.

Objetivo del estudio:

Informar sobre la primera aplicación de metalloenaminas derivadas de las N-sulfinil iminas.
Para lograr una adición altamente diastereoselectiva a los aldehídos.

Principales métodos:

Reacción de las metalloenaminas con los aldehídos.
Reducción estereoselectiva de las iminas beta-hidroxi-N-sulfinilo intermedias utilizando catecolborano y LiBHEt3.

Principales resultados:

Se logró una adición altamente diastereoselectiva de metalloenaminas a los aldehídos.
Se obtuvieron derivados de alcoholes sin- y anti-1,3-amino con proporciones diastereoméricas muy altas.

Conclusiones:

Este estudio presenta un método novedoso y eficiente para sintetizar derivados de alcohol de 1,3-amino.
La metodología ofrece un excelente control estereoquímico, lo que produce valiosos bloques de construcción quirales.

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