Dois ligantes C 2 -simétricos bis(sulfonamide) contendo o fluoreno-quiral (1R,2R)-ciclohexano-1,2-diamina foram complexados com Rh III (Cp*) e usados como catalizador para redução aromática de cetonas. Os alcoois secundários correspondentes foram obtidos com ee 87-100% e rendimento de 85-99%, sob condições de transferência de hidrogenio assimétrica (THA), usando formato de sodio aquoso como fonte de hidretos. Usando acetofenona, obteve-se ee de 94% e rendimento de 86-97%, com uma razão substrato/catalizador de 10.000.Two C 2 -symmetric bis(sulfonamide) ligands containing fluorene-chiral (1R,2R)-cyclohexane-1,2-diamine were complexed to Rh III (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.

Two quinazolinediones were crystallized and the molecular structures solved by monocrystal X-ray diffraction analysis. The title compounds include the only variation of the -OMe substituent at orto or meta positions of the aromatic ring. The results were contrasted with the analogous para substituted derivative allowing a complete structural comparison in order to see the substituent effect. The formation of different hydrogen bonding motifs was observed which are relevant to the design of supramolecular assemblies.