Iron catalysts have been developed in our lab that are highly efficient for the asymmetric hydrogenation of prochiral ketones and imines to the corresponding enantioenriched alcohols and amines, respectively by transfer of hydrogen from the solvent isopropanol. Some of these are of value in the pharmaceutical and fine chemical industry. Our progress in this area will be discussed from the time of the initial discovery of activity of the trans-[Fe(CO)(P,N,N,P)(NCMe)]2+ complexes in 2007 where P,N,N,P represents a tetradentate ligand with phosphine and imine donors.1 Studies of the mechanism of action have led to the recent development of enzyme-like catalysts with turn-over frequencies exceeding 100 s-1 at 30 degrees.2,3 The active species are thought to have interesting iron hydride and eneamido structures that allow the metal and ligand to cooperate in the easy reduction of the substrate. The mechanistic studies also led us to the discovery of iron nanoparticles capable of catalytic asymmetric transfer hydrogenation and alcohol oxidation.4,5 Progress in the development of iron catalysts for the asymmetric pressure hydrogenation of ketones and imines will also be discussed.1,61 Sui-Seng, C.; Freutel, F.; Lough, A. J.; Morris, R. H. Angew. Chem. Int. Ed. Engl. 2008  , 47, 940-943. 2 Mikhailine, A. A.; Maishan, M. I.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2012  , 134, 12266-12280.. 3 Zuo, W.; Morris, R. H. in progress. ?4?Sonnenberg, J. F.; Pichugin, D.;Coombs, N.; Morris, R. H. Topics in Catalysis 2013  , in press; Sonnenberg, J. F.; Coombs, N.; Dube, P. A.; Morris, R. H. J. Am. Chem. Soc. 2012  , 134, 5893-5899. 6Lagaditis, P. O.; Sonnenberg, J. F.; Morris, R. H. in progress.

Iron catalysts for the asymmetric reduction of ketones and imines

246th National Meeting (2013)

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