The first organocatalyzed sulfoxidation reaction towards enantioenriched (R)-modafinil (Armodafinil®), a drug against narcolepsy, is reported here. A series of chiral organocatalysts, e.g., different chiral BINOL-phosphates, or a fructose-derived N-substituted oxazolidinone ketone (Shi catalyst) were applied for the sulfoxidation reaction with environmentally friendly H2O2 as a convenient oxyge...

A bioluminescent clinical isolate of Streptococcus pneumoniae was used to test the real-time effects of the oxazolidinone antibiotic, linezolid, on metabolism compared with effects on cell replication. Viable counts and bioluminescence measurements showed that linezolid has little bactericidal effect, which was similar at minimum (6 mg/L), intermediate (13 mg/L) and maximum (20 mg/L) serum conc...

5-Thiourea and 5-dithiocarbamate oxazolidinones were synthesized as a continuation of research on 5-thiocarbonyl oxazolidinone antibacterial agents considering the hydrophobic parameters of the molecule. The structure-activity relationship (SAR) study revealed that the antibacterial activity on 5-thiocarbonyl oxazolidinones was significantly affected by the lipophilicity, especially the calcula...

The principle of Le Chatelier was used in demonstrating that 3-chloro-4,4-dimethyl-2-oxazolidinone (compound 1) itself kills Staphylococcus aureus rather than the very small amount of free chlorine in hydrolysis equilibrium with compound 1. On the other hand, when the N-bromo analog of compound 1 (compound 1B) was used as the disinfectant, the mixture of combined compound 1B and free bromine fo...

Dye-exchanged Y zeolite is shown to be an effective medium to control the stereoselectivity in the photooxygenation of chiral oxazolidinone-functionalized Z/E-1 enecarbamates. An enantioselectivity (ee) as high as 80% was observed in the methyldesoxybenzoin (MDB) product, obtained in the methylene-blue-exchanged NaY zeolite at room temperature. The efficacy of the asymmetric induction in the MD...

Oxazolidinone-functionalized enecarbamates react stereoselectively with singlet oxygen to give methyldesoxybenzoin (MDB) in moderate to high enantiomeric excess. The stereochemical outcome depends on the E/Z substrate geometry, temperature, and solvent variables. The analysis of the differential activation parameters suggests a large contribution from the entropy term in determining the enantio...