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