Enantioselective formation of arene oxides by direct oxidation of the arene.
Polycyclic aromatic compounds may be metabolized in humans to materials which are carcinogenic. These metabolites frequently contain an arene oxide group which is implicated in binding the metabolite to important biological substrates such as DNA. These enzymatic processes produce arene oxides in a highly enantioselective fashion. Direct oxidation of arenes by typical oxidants gives racemic oxide. We have been interested in converting arenes to arene oxides by direct oxidation in an enantioselective reaction. Three oxidation systems have been used to convert a variety of polycyclic aromatic compounds to arene oxides in processes which gives modest enantiomeric excesses.
Murray
R W
RW
Department of Chemistry, University of Missouri-St. Louis, St. Louis, MO 63121, USA. aidan@admiral.umsl.edu
Singh
M
M
D002384:Catalysis; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013057:Spectrum Analysis; D013237:Stereoisomerism
D011083:Polycyclic Compounds