Wednesday, June 25, 2008
Congressional Room (Capital Hilton)

2008 BREEN FELLOWSHIP RECIPIENT: Biocatalytic Approaches to the Asymmetric Oxidation of Sulfides and Alkenes

Antonio Osorio-Lozada and Horacio F. Olivo. The University of Iowa, Iowa City, IA

Oxidation reactions are considered one of the transformations causing the most environmental footprint. Our group is interested in developing green processes to carry out oxidative transformations incorporating biocatalysts. We are interested in developing microbial and chemo-enzymatic processes that are attractive to the chemical and pharmaceutical industries. Asymmetric oxidations are of particular interest in developing chiral molecules for enantioselective syntheses.

Modafinil is a unique CNS stimulant that lacks any addiction liability. We developed a very short enantioselective route to one of its enantiomers. This new route employs microorganisms containing oxidative enzymes capable to deliver a desired sulfoxide in a highly enantioselective manner. Currently, modafinil is being investigated for the treatment of cocaine and metamphetamine addicts, and in the treatment of ADHD.

Our group is also currently developing an asymmetric chemo-enzymatic oxidation of alkenes. Epoxidation of indene is of particular interest to our group. Indene oxide is a valuable starting material for the syntheses of indinavir (Merck's HIV protease inhibitor), several chiral catalysts (Jacobsen's Cr(III) Schiff base), and also for the synthesis of a new chiral auxiliary developed in our group. Having a green asymmetric epoxidation process of indene will be attractive to the chemical and pharmaceutical industries. We will present two successful applications of green chemistry principles in the efficient preparation of useful compounds for synthetic and medicinal chemists.