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Disimetría electrónica en el reconocimiento quiral.

Seth N Brown¹, Everett T Chu, Michael W Hull

¹Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA. Seth.N.Brown.114@nd.edu

Journal of the American Chemical Society

|November 17, 2005

Resumen

Los complejos de titanio con ligandos beta-diketonato exhiben disimetría electrónica, lo que permite el reconocimiento quiral. Este efecto electrónico, no el obstáculo estérico, impulsa la diastereoselectividad en los complejos de titanio-BINOL.

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Área de la Ciencia:

Química organometálica Química orgánica de los metales.
Coordinación Química de la Coordinación
La estereoquímica es la estereoquímica.

Sus antecedentes:

Los ligandos beta-dicetonato en los complejos de titanio simétricos C2 crean disimetría electrónica.
El LUMO (Lowest Unoccupied Molecular Orbital) es un orbital inclinado dz2, influenciado por la configuración del titanio.

Objetivo del estudio:

Para investigar el papel de la disimetría electrónica en el reconocimiento quiral.
Para sondear la diastereoselectividad de los complejos titanio-BINOL.

Principales métodos:

Síntesis de complejos de titanio-beta-diketonato con el 1,1'-bi-2-naftholato (BINOL).
Espectroscopia de Resonancia Magnética Nuclear (RMN) para determinar las relaciones diastereoméricas.
Cristalografía de complejos relacionados para establecer la estereoquímica.

Principales resultados:

Los complejos de titanio-BINOL formaron exclusivamente un diastereómero, como lo predijeron los factores electrónicos.
La cristalografía confirmó la predicción de la estereoquímica basada en fundamentos electrónicos.
Los análogos de estaño mostraron una diastereoselectividad significativamente más baja, lo que apoya el control electrónico.

Conclusiones:

La disimetría electrónica en los complejos de titanio es crucial para el reconocimiento quiral.
La diastereoselectividad observada se rige principalmente por efectos electrónicos, no por factores estéricos.