ASYMMETRIC TRANSFER HYDROGENATION OF KETONES IN AQUEOUS SOLUTION CATALYZED BY RHODIUM (III) COMPLEXES WITH C2-SYMMETRIC FLUORENE-LIGANDS CONTAINING CHIRAL (1R, 2R)-CYCLOHEXANE-1, 2-DIAMINE

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

ASYMMETRIC TRANSFER HYDROGENATION OF KETONES IN AQUEOUS SOLUTION CATALYZED BY RHODIUM (III) COMPLEXES WITH C2-SYMMETRIC FLUORENE-LIGANDS CONTAINING CHIRAL (1R, 2R)-CYCLOHEXANE-1, 2-DIAMINE

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

URI: http://dspace.uan.mx:8080/jspui/handle/123456789/1970

Fecha: 2010

Resumen:

Dos ligandos de bis(sulfonamida) simétricos C2 que contienen flúor quiral (1R,2R)-ciclohexano-1,2-diamina fueron complejados a RhIII(Cp*) y usados como catalizador para reducir las cetonas aromáticas. Los correspondientes alcoholes secundarios quirales se obtuvieron en condiciones de hidrogenación por transferencia asimétrica (ATH) en un 87-100% de ee y 85-99% de rendimiento, utilizando como fuente de hidruros al formiato de sodio acuoso. Con acetofenona, el 94% de ee y el 86-97% de rendimiento se logró con una relación 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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