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NOYORI Molecular Catalysis
Research Director: Dr.Ryoji Noyori
(Professor School of Science Nagoya University)

Research Term 1991〜1996
Outline of Research Results

 Guided by the theme "from ready-made to tailor-made catalysts", this project focused on efficient reactions which can make both right- and left-handed molecules, either large or small, natural or synthetic, with high enantiomeric purity. It also examined catalysts for the synthesis of stereo-regular polymers in which all of the chains are the same length. Strong emphasis was placed on the efficient synthesis of bio-active compounds, since many active sites interact with molecules through molecular recognition, where matching of chirality plays a key role. In all of this research activity the basic strategy involved synthesizing well-shaped organic compounds, then attaching them to a central metal; it was thus possible to control the reactivity of the central metal through such a coordination of the organic ligand. High purity at the molecular level provides significant power to create new functions and materials.

Research Results

Hydrogenation of supercritical carbon dioxide: Supercritical carbon dioxide can be hydrogenated rapidly with Ru(II) complex catalysts to afford formic acid, methyl formate, and dimethylformamide in high yield.

Asymmetric hydrogenation in supercritical fluids: Supercritical carbon dioxide or flons are usable as reaction media for highly selective asymmetric hydrogenation of certain olefins catalyzed by chiral transition metal complexes.

Practical hydrogenation of ketones: A Ru-phosphine-1,2-diamine combined catalyst effects hydrogenation of C=O function preferentially over coexisting C=C or CzC linkage. This new hydrogenation is very rapid and highly productive, and is superior to any existing metal hydride reactions. This method exhibits promise for the practical synthesis of a wide range of important alcoholic compounds.

Stereoselective hydrogenation of ketones: Proper selection of the phosphine and diamine ligands in the Ru-phosphine-1,2-diamine catalyst allows highly efficient hydrogenation of chiral and achiral ketones with unprecedented diastereo- or enantioselectivity. The technical applicability is enormous.

Asymmetric transfer hydrogenation of ketones and imines: Newly designed Ru(II) complexes having arene and chiral 1,2-diamine auxiliaries effect the highly enantioselective reduction of ketones or imines using 2-propanol or formic acid as a hydrogen donor. A wide array of alcohols and amines of high optical purity are accessible.

Living, stereospecific polymerization of phenylacetylenes: Organo-rhodium(I) complexes possessing phosphoine and diene ligands initiate polymerization of phenylacetylenes in a living and stereospecific manner. This method allows the synthesis of the homo- and block-polymer with a narrow dispersity.


·Illustration of the differences between a homogeneously catalyzed-liquid phase reaction (Left), a heterogeneously Catalyzed-gas phase reaction (Right), and a homogeneously catalyzed-supercritical phase reaction (Center).



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