Download - Noyori asymmetric hydrogenation
Aida Suraya Azzuhri2 0 1 0 6 6 3 4 1 8
Nor Zulfa binti Tahir2 0 0 9 7 1 3 1 3 1
Nurhafizah Mohd Salleh2 0 0 9 9 2 5 8 5 5
NOYORI
ORGANOMETALLIC CHEMISTRY CHM676 PROF DR HADARIAH
INTRODUCTION
BIOGRAPHICAL OF
RYOJI NOYORI
RYOJI NOYORI
•Born : on September 3, 1938•in a suburb of Kobe (now Ashiya), Japan•the first son of Kaneki and Suzuko Noyori
ACHIEVEMENT
•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
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
NOYORI CATALYSTS
MECHANISM
EXAMPLE:
NOYORI ASYMMETRIC HYDROGENATION
ASSYMETRIC HYDROGENATION 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
NOYORI ASSYMETRIC HYDROGENATION
ASYMMETRICAL ?
chemical reaction for the enantioselective hydrogenation of ketone, aldehydes, and imines.
NOYORI CATALYSTS
MECHANISM
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
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.).
• 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.
• An antipsychotic agent BMS 181100 is synthesized using BINAP/diamine-Ru catalyst.
REFERENCES
• http://www.chem.harvard.edu/groups/myers/handouts/22_Noyori_Asymmetric_Hydrog.pdf
• http://www.synarchive.com/named-reactions/Noyori_Asymmetric_Hydrogenation
RYOJI NOYORI