Noyori asymmetric hydrogenation

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application, background and mechanisms

Text of Noyori asymmetric hydrogenation

  • 1. INTRODUCTION BIOGRAPHICAL OF RYOJI NOYORI

2. Born : on September 3, 1938 in a suburb of Kobe (now Ashiya), Japan the first son of Kaneki and Suzuko Noyori RYOJI NOYORI won the Nobel Prize in Chemistry in 2001 He shared the prize of study of chirally catalyzed hydrogenations WITH William S. Knowles ; the 2nd half went to K. Barry Sharpless for his study in chirally catalyzed oxidation reactions Prize motivation: "for their work on chirally catalysed hydrogenation reactions. Field: Organic chemistry, industrial chemistry ACHIEVEMENT 3. RESEARCH Noyori believes strongly in the power of catalysis and of green chemistry Noyori is most famous for asymmetric hydrogenation using as catalysts complexes of rhodium and ruthenium, particularly those based on the BINAP ligand. Asymmetric hydrogenation of an alkene in the presence of ((S)- BINAP)Ru(OAc)2 is used for the commercial production of enantiomerically pure (97% ee) naproxen, used as an anti-inflammatory drug. The antibacterial agent levofloxacin is manufactured by asymmetric hydrogenation of ketones in the presence of a Ru(II) BINAP halide complex. He has also worked on other asymmetric processes. Each year 3000 tones (after new expansion) of menthol are produced (in 94% ) by Takasago International Co., using Noyori's method for isomerization of allylic amines 4. NOYORI CATALYSTS 5. MECHANISM 6. EXAMPLE: 7. NOYORI ASYMMETRIC HYDROGENATION ASSYMETRICHYDROGENATION chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three dimensional spatial selectivity. characterized by asymmetry in the spatial arrangement or placement of parts or components. THEREFORE NOYORIASSYMETRICHYDROGENATION ASYMMETRICAL ? chemical reaction for the enantioselective hydrogenation of ketone, aldehydes, and imines. 8. NOYORI CATALYSTS 9. MECHANISM 10. Noyori asymmetric hydrogenation. Chemical reaction for the enantioselective hydrogenation of ketones, aldehydes and imines. BINAP-Ru catalyst functionalized ketones. BINAP/diamine-Ru catalyst simple ketones. Used in production of several drugs, such as the antibacterial levofloxin, the antibiotic carbapenem and the antipsychotic agent BMS181100. APPLICATION 11. Industrial application An antibacterial levofloxacin is synthesized using (R)-1,2-propandiol, which is synthesized from hydroxyacteone using Noyori asymmetric hydrogenation(Takasago Co./Daiichi Pharmaceutical Co.). 12. An antibiotic carbapenem is also prepared using Noyori asymmetric hydrogenation via (2S,3R)-methyl 2-(benzamidomethyl)-3- hydroxybutanoate, which is synthesized from racemic methyl 2-(benzamidomethyl)-3- oxobutanoate by dynamic kinetic resolution. 13. An antipsychotic agent BMS 181100 is synthesized using BINAP/diamine-Ru catalyst. 14. REFERENCES http://www.chem.harvard.edu/groups/myers/ handouts/22_Noyori_Asymmetric_Hydrog.pdf http://www.synarchive.com/named- reactions/Noyori_Asymmetric_Hydrogenation

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