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• 108-98-5 thiophenol 
• 17277-58-6 methyl (phenylsulfanyl)acetate 
• 14090-83-6 methyl 2-phenylsulfinylacetate 

Relevant academic research and scientific papers

Electrochemical enzymatic deoxygenation of chiral sulfoxides utilizing DMSO reductase

Preparation of enantiomerically enriched sulfoxides by an electrochemical enzymatic system utilizing DMSO reductase was studied. This system consists of a glassy carbon electrode as the working electrode, methyl viologen as the mediator and DMSO reductase

Chemistry of oxaziridines. 17. N-(phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine: A highly efficient reagent for the asymmetric oxidation of sulfides to sulfoxides

The synthesis, structure, and enantioselective oxidations of a new chiral N-sulfonyloxaziridine 12c [3,3-dichloro-1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2, 3'-oxaziridine]] are reported. This oxidant, which exhibits remarkably high and predictable ee's for the enantioselective oxidation of prochiral sulfides to sulfoxides, is prepared in three steps from (+)- or (-)-camphor in 50% overall yield. Steric effects are primarily responsible for the molecular recognition and are predictable using a simple active-site model where the nonbonded interactions between the RL and RS groups of the sulfide (RL-S-RS) and the active-site surface are minimized in a planar transition-state structure. The fact that alkyl aryl sulfides give high ee's in nonpolar solvents suggests that there is also a stereoelectronic component to the molecular recognition. High ee's (>90%) are anticipated for those sulfides where the difference in size of the groups directly bonded to the sulfur atom is large, i.e., aryl, tert-butyl vs CH2R (R = H, alkyl, benzyl, etc). The X-ray structure and studies with the dihydro, difluoro, and dibromo oxaziridines 12a, 12b, and 12d reveal that the exceptional enantioselectivities displayed by 12c are a consequence of a molecular cleft or groove, defined by the oxaziridine chlorine atoms and phenylsulfonyl group, on the active-site surface.

A FACILE ROUTE TO HOMOCHIRAL SULFOXIDES

Biocatalytic resolution of methyl sulfinylacetates afford sulfoxides (R)-(1)-(6) in very high optical yields; the products have been used in a systematic study of the "SPAC" reaction, an asymmetric synthesis of γ-hydroxy-α,β-unsaturated esters.

ENZYME MEDIATED SYNTHESIS OF OPTOCALLY ACTIVE ο-ARENESULFINYLALKANOIC ESTERS

Incubation of methyl arenesulfinylacetates and methyl α-benzenesulfinylpropionate with Corynebacterium equi IFO 3730 afforded the corresponding chiral sulfoxides of high optical purites in moderate to good chemical yields.