Electrochemical enzymatic deoxygenation of chiral sulfoxides utilizing DMSO reductase

The first non-turnover voltammetric response from a molybdenum enzyme: direct electrochemistry of dimethylsulfoxide reductase from Rhodobacter capsulatus

“…It has been shown that DMSO reductase is capable of enantioselective reduction of racemic mixtures of chiral sulfoxides in the presence of photochemically or electrochemically reduced mediators [17,18]. However, direct electrochemistry of the Mo active site of the DMSO reductase family, and of mononuclear Mo enzymes in general, has remained elusive.…”

Unconventional Biocatalytic Approaches to the Synthesis of Chiral Sulfoxides

“…first described the use of DmsABC from Rhodobacter sphaeroides f. s. denitrificans for the kinetic resolution of the non‐endogenous methyl phenyl sulfoxide, obtaining ( R )‐methyl phenyl sulfoxide in 42 % yield and 97 % ee [33] . Following this initial work, the substrate scope of this biotransformation was further expanded to a variety of alkyl‐aryl‐sulfoxides [34–36] . In 2004, Luckarift et al.…”

“…[33] Following this initial work, the substrate scope of this biotransformation was further expanded to a variety of alkylaryl-sulfoxides. [34][35][36] In 2004, Luckarift et al described the kinetic resolution of chiral sulfoxides with opposite stereoselectivities depending on the species of anaerobic bacteria used [37] (Scheme 6). A total of seven organisms used as whole cell biocatalysts were exposed to 6.5 mM (1 g L À 1 ) rac-14 and it was found that E. coli, Proteur vulgaris, Serratia sp., Citrobacter braakii and Halobacterium halobium selectively reduced the R enantiomer while Rhodobacter capsulatus and Klebsiella sp.…”

ZrCl4/NaI and ZrOCl2 · 8H2O/NaI as effective systems for reductive coupling of sulfonyl chlorides and chemoselective deoxygenation of sulfoxides

“…We have also applied ZrCl 4 /NaI and ZrOCl 2 · 8H 2 O/NaI for the chemoselective reduction of sulfoxides to their sulfides under mild conditions (scheme 1b). Reduction of sulfoxides which are used as chiral auxiliaries for the synthesis of chiral organic molecules is also an important transformation [52][53][54][55][56][57][58][59]. SCHEME 1…”