| Abstract: | A variety of bacteria, yeasts and fungi were screened for the preparation of enantiomers of chiral sulfoxides from aryl-aryl or alkyl-aryl (E) and (Z) vinyl sulfides 1. The asymmetric oxidation was studied on a model substrate, (E)-methyl-(2-phenyl)-vinylsulfide la. Along with various amounts of sulfone, all strains tested gave the corresponding sulfoxide, optically active, albeit with different chemical and optical yields. The stereochemical outcome of the reaction appears to be quite invariant and both enantiomers can be obtained. The high sensitivity towards substrate structure observed in a variety of sulfides is related to the toxicity of the substrates and the microbial oxidation is therefore assumed to be a detoxication reaction. |
