ASYMMENTRIC TRANSFER HYDROGENATION IN AQUEOUS SOLUTION CATALYZED BY RHODIUM COMPLEXES WITH C2-SYMMETRIC FLOURENCE-LIGANS CONTAINING CHIRAL (1R, 2R)-CYCLOHEXANE-1, 2-DIAMINE

CHAVEZ, DANIEL; PARRA HAKE, MIGUEL; AGUIRRE, GERARDO; SOMANATHAN, RATNASAMY; MONTALVO GONZALEZ, RUBEN

ASYMMENTRIC TRANSFER HYDROGENATION IN AQUEOUS SOLUTION CATALYZED BY RHODIUM COMPLEXES WITH C2-SYMMETRIC FLOURENCE-LIGANS CONTAINING CHIRAL (1R, 2R)-CYCLOHEXANE-1, 2-DIAMINE

CHAVEZ, DANIEL; PARRA HAKE, MIGUEL; AGUIRRE, GERARDO; SOMANATHAN, RATNASAMY; MONTALVO GONZALEZ, RUBEN

URI: http://dspace.uan.mx:8080/jspui/handle/123456789/277

Fecha: 2010

Resumen:

Dos complejos bis (sulfonamida) simétricos en C2 que contenían (1R, 2R) -ciclohexano-1,2-diamina fluoreno-quiral se complejaron a RhIII (Cp *) y se usaron como catalizadores para reducir cetonas aromáticas. Los correspondientes alcoholes secundarios quirales se obtuvieron en 87-100% de ee y 85-99% de rendimiento, en condiciones de hidrogenación de transferencia asimétrica (ATH) usando formiato de sodio acuoso como fuente de hidruro. Con acetofenona, se obtuvo un 94% de ee y un rendimiento de 86-97% con una relación de sustrato / catalizador (S / C) de 10.000.

Descripción:

Two C2-symmetric bis(sulfonamide) ligands containing fluorene-chiral (1R,2R)-cyclohexane-1,2-diamine were complexed to RhIII(Cp*) and used as catalyst to reduce aromatic ketones. The corresponding chiral secondary alcohols were obtained in 87-100% ee and 85-99% yield, under asymmetric transfer hydrogenation (ATH) conditions using aqueous sodium formate as the hydride source. With acetophenone, 94% ee and 86-97% yield was achieved with substrate/catalyst (S/C) ratio of 10,000.

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