application, background and mechanisms

2. INTRODUCTION
BIOGRAPHICAL
OF
RYOJI NOYORI

3. •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

4. 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

5. NOYORI CATALYSTS

6. MECHANISM

7. EXAMPLE:

8. 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.

9. NOYORI CATALYSTS

10. MECHANISM

11. 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

13. 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.).

14. • 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.

15. • An antipsychotic agent BMS 181100 is
synthesized using BINAP/diamine-Ru catalyst.

16. REFERENCES
• http://www.chem.harvard.edu/groups/myers/
handouts/22_Noyori_Asymmetric_Hydrog.pdf
• http://www.synarchive.com/named-
reactions/Noyori_Asymmetric_Hydrogenation