112456-62-9

Upstream product

• 123-09-1 4-chlorophenyl methyl sulfide 
• 934-73-6 methyl 4-chlorophenyl sulfoxide 
• 3085-42-5 bis(4-chlorophenyl)sulfoxide 
• 676-58-4 methylmagnesium chloride 
• 164021-74-3 (1S,2R)-(-)-2-[N-(3’,5’-di-tert-butylsalicylidene)amino]-1,2-diphenylethanol 
• 106-54-7 p-Chlorothiophenol 
• 35559-38-7 2-[(4-chlorophenyl)sulfanyl]ethyl phenyl sulfone 
• 1308833-72-8 2-[(4-chlorophenyl)sulfinyl]ethyl phenyl sulfone 
• 74-88-4 methyl iodide 
• 75-16-1 methylmagnesium bromide 
• 917-64-6 methyl magnesium iodide 
• 66789-19-3 menthyl (S_c,S_c)-p-chlorobenzenesulfinate 

Downstream Products

• 125416-27-5 10-dicyclohexylsulfamoyl-D-isobornyl (S)(-)-4-chlorophenylsulfinylacetate 

Relevant academic research and scientific papers

Asymmetric catalytic sulfoxidation by a novel v IV 8 cluster catalyst in the presence of serum albumin: A simple and green oxidation system

A novel VIV8 cluster formulated as [V8O12(OH)4(CH3O)4(DAC)4]·7CH3OH (1) (DAC = 1,2-diaminocyclohexane) has been constructed successfully. Enantioselective oxidation of a series of alkyl aryl sulfides catalyzed by 1 is tested in an aqueous medium in the presence of serum albumin. The catalytic procedure is found to be simple and environmentally friendly. The influences of the parameters such as concentration of catalyst and oxidant, pH, and reaction time on the thioanisole as models are investigated. Under optimum conditions, 1 exhibits high conversion (up to 99%), excellent chemoselectivity (≥90% in all cases) and moderate enantioselectivity (up to 75% ee). After binding with serum albumin, the catalytic activity of 1 is promoted. The bovine serum albumin (BSA) and pig serum albumin (PSA) molecules have a more positive effect on the catalytic activity.

An efficient silica supported Chitosan@vanadium catalyst for asymmetric sulfoxidation and its application in the synthesis of esomeprazole

A new type of silica supported Chitosan@vanadium complex was used as a highly active heterogeneous catalyst for asymmetric oxidation of aryl alkyl sulfides. With the economic aqueous H2O2(30%) as the oxidant, the oxidation products were obtained in high yields (up to 95%) with good enantioselectivities (up to 68% ee). It is noted that the marketed drug Nexium (first proton-pump inhibitor, esomeprazole) could be synthesized easily by the newly developed asymmetric sulfoxidation reaction. In addition, the highly active catalyst can be reused five times without losing its catalytic activity.

Altering 2-Hydroxybiphenyl 3-Monooxygenase Regioselectivity by Protein Engineering for the Production of a New Antioxidant

2-Hydroxybiphenyl 3-monooxygenase is a flavin-containing NADH-dependent aromatic hydroxylase that oxidizes a broad range of 2-substituted phenols. In order to modulate its activity and selectivity, several residues in the active site pocket were investigated by saturation mutagenesis. Variant M321A demonstrated altered regioselectivity by oxidizing 3-hydroxybiphenyl for the first time, thus enabling the production of a new antioxidant, 3,4-dihydroxybiphenyl, with similar ferric reducing capacity to the well-studied piceatannol. The crystal structure of M321A was determined (2.78 ?), and molecular docking of the 3-substituted phenol provided a rational explanation for the altered regioselectivity. Furthermore, HbpA was found to possess pro-S enantioselectivity towards the production of several chiral sulfoxides, whereas variant M321F exhibited improved enantioselectivity. Based on the biochemical characterization of several mutants, it was suggested that Trp97 stabilized the substrate in the active site, Met223 was involved in NADH entrance or binding to the active site, and Pro320 might facilitate FAD movement.

A convenient approach to chiral sulfoxides by enantioselective oxidation with a steroidal furylhydroperoxide

The introduction of a steroidal residue into a position distant from the reaction center shows a beneficial effect on the reactivity of secondary furylhydroperoxides: chiral sulfoxides are obtained by asymmetric oxidation of sulfides and/or kinetic resolution of racemic sulfoxides with reduced reaction times and high enantiomeric excesses.

Substituent effects and mechanism elucidation of enantioselective sulfoxidation catalyzed by vanadium Schiff base complexes

The effects of substituents of the Schiff base ligands on oxovanadium-catalyzed enantioselective sulfoxidation were first systematically studied, and a rational mechanism of enantioselective sulfoxidation based on our experimental data and the reported da

Sulfide oxidation catalyzed vanadyl complexes of N-salicylidene α-amino acids at low catalyst loading

Sulfoxides are extensively used in chemical and pharmaceutical industries. Various catalytically synthetic methods were reported, but in common 1-10 (mol)% catalyst loading were demanded. Sulfide oxidation catalyzed by vanadyl complexes of N-salicylidene α-amino acids with catalyst loading as low as 0.03 (mol)% gave high yields at room temperature with aqueous hydrogen peroxide as an oxidant, which is a green, solvent-free, energy-saving and easy-operated protocol. In contrast, vanadyl complexes of N-salicylidene amino alcohols could not, even at 0.1 (mol)%. The possible reason is that the stronger acidity of N-salicylidene α-amino acids makes their vanadyl complexes stable to aqueous hydrogen peroxide. This rule may be used in designing other high efficient catalysts, especially with aqueous hydrogen peroxide as an oxidant.

Reactivity of furylhydroperoxides in asymmetric oxidation and kinetic resolution

Furylhydroperoxides can be successfully employed in the enantioselective oxidation of allylic alcohols and sulfides under Sharpless-type conditions. Their kinetic resolution provides a mean both to chiral furylhydroperoxides and furylalcohols.

Stereoselective sulfoxidation catalyzed by achiral Schiff base complexes in the presence of serum albumin in aqueous media

Four coordination complexes ML derived from an achiral Schiff base ligand (H2L = 2,2′-[(1,2-ethanediyl)bis(nitrilopropylidyne)]bisphenol) have been synthesized and characterized. A method is described for the enantioselective oxidation of a series of aryl alkyl sulfides using the coordination complexes in the presence of serum albumins (SAs) in an aqueous medium at ambient temperature. The mixture of metal complexes with serum albumins is useful for inducing asymmetric catalysis. The complex, albumin source and substrate influence stereoselective sulfoxidation. At optimal pH with the appropriate oxidant, some of ML/SA systems are identified as very efficient catalysts, giving the corresponding sulfoxides in excellent chemical yield (up to 100%) and good enantioselectivity (up to 94% ee) in certain cases. UV–visible spectroscopic data provide evidence that stronger binding between the complex and serum albumin lead to higher enantioselectivity.

Synthesis of a renewable hydroperoxide from (+)-norcamphor: Influence of steric modifications of the bicyclic framework on asymmetric sulfoxidation

A renewable tertiary hydroperoxide has been efficiently synthesized in 83% overall yield starting from commercially available (+)-endo-2-norborneol. This oxygen donor, derived from (+)-norcamphor, when employed in Ti(Oi-Pr) 4-catalyzed sulfoxidations, proved to be considerably more reactive when compared to a previously reported camphor-derived hydroperoxide. Reduced steric hindrance of the new oxidant lowered the level of asymmetric induction achieved in the oxidation, but stereoconvergent kinetic resolution has been exploited to improve enantioselectivity. Excellent recovery (95%) of the tertiary alcohol at the end of the sulfoxidation provides a highly advantageous chiral resource saving protocol.

Kinetic resolution and asymmetric oxidation as combined routes to chiral sulfoxides

Non-racemic sulfoxides are accessible through a modified Sharpless kinetic resolution of racemic sulfoxides. Furthermore, thanks to enantioconvergence of asymmetric oxidation and kinetic resolution a successful improvement of e.e. is achievable.