2844-08-8

Upstream product

• 7417-73-4 benzyl t-butyl sulfide 
• 126494-96-0 2,2-diphenyl-1,2-dihydroxypropyl 2-O-tert-butylsulfinate 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 41047-23-8 C₁₁H₁₅⁽²⁾HOS 
• 107383-10-8 C₁₁H₁₅⁽²⁾HO₂S 

Relevant academic research and scientific papers

Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides

Steric and electronic effects in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast, the benzyl substituent can be replaced by sterically comparable groups with no effect on enantioselectivity. Copper-mediated oxidation of substituted aryl benzyl sulfides display modest steric and electronic effects resulting in comparable or lower enantioselectivities to those obtained with the unsubstituted benzyl phenyl sulfide.

Diastereomeric sulfinates derived from (L)-N-methylephedrine: Synthesis, applications and rearrangements

The reaction of sulfinyl chlorides with (L)-N-methylephedrine alone or in the presence of tertiary amines was found to produce diastereomeric sulfinates with diastereomeric purities up to 90%. The diastereomeric ratio is strongly influenced by the nature

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 General Route to Enantiomerically Pure Sulfoxides from a Chiral Sulfite

Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate.This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselecti

Microbial oxidation of benzyl sulfides and bibenzyl by Mortierella isabellina and Helminthosporium species

The biotransformation of 1,2-diphenylethane by the fungus Mortierella isabellina ATCC 42613, and that of a series of alkyl benzyl sulfides by the fungi M. isabellina and Helminthosporium species NRRL 4671 have been studied.Mortierella hydroxylates 1,2-diphenylethane in low yield, giving (S)-1,2-diphenylethanol with an enantiomeric purity of 33percent.Bioconversions of deuterium-labelled and racemic 1,2-diphenylethanol by M. isabellina demonstrate that this organism performs reversible oxidation/reduction of the alcohol.Biotransformations of n-alkyl benzyl sulfides by H. species give predominatly the (S) enantiomer of sulfoxide, with no sulfone formation, but M. isabellina, although showing a general preference for the oxidation of alkyl benzyl sulfides to (R) sulfoxides, also generates sulfones from n-alkyl benzyl sulfides in a time-dependent manner that suggests a stereoselective removal of (R) sulfoxide.The latter microorganism can be used, however, for the production of (R)-benzyl methyl and benzyl isopropyl sulfoxides, and gives (S)-benzyl tert-butyl sulfoxide in low yield. Key words: biotransformation, enzymes, sulfoxides.

Stereochemistry of Oxygenation of Organic Sulphides with Pig Liver Microsomal FAD-containing Mono-oxygenase: Comparison with Cytochrome P-450PB Oxidations

The enantiotopic differentiating ability of pig liver microsomal FAD-containing mono-oxygenase (EC 1.14.13.8) in the oxygenation of nine unsymmetrical sulphides has been investigated.By this enzymatic oxygenation, the sulphides are converted into the corr