114129-50-9

Upstream product

• 35330-76-8 2-methanesulfinylnaphthalene 
• 7433-79-6 2-methylthionaphthalene 
• 91-60-1 2-Naphthalenethiol 
• 1308833-67-1 2-(naphthylsulfinyl)ethyl phenyl sulfone 
• 74-88-4 methyl iodide 
• 1308834-02-7 2-(2-naphthylsulfanyl)ethyl phenyl sulfone 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 35330-76-8 2-methanesulfinylnaphthalene 

Relevant academic research and scientific papers

Titanium-Catalyzed, Asymmetric Sulfoxidation of Alkyl Aryl Sulfides with Optically Active Hydroperoxides

The Ti-catalyzed, asymmetric oxidation of alkyl aryl sulfides by enantiomerically pure hydroperoxides (ee >99%) has been examined. Enantioselectivities with ee values up to ca. 80% were achieved for the oxygen transfer from (S)-(-)-1-phenylethyl hydroperoxide 2a to methyl phenyl and methyl p-tolyl sulfide 1a in CCl4 as solvent, but with much overoxidation to the corresponding sulfone 4. Detailed mechanistic studies showed that the enantioselectivity of the sulfide 1a oxidation results from a combination of a rather low (ee values >20%) asymmetric induction in the sulfoxidation and an effective kinetic resolution (ee values ca. 80% at 85% sulfide conversion) of the sulfoxide 3a by enantioselective oxidation to the sulfone 4a. The overoxidation (loss of chemoselectivity) is due to sulfoxide coordination to the Ti metal to generate a template in which the oxygen atom is intramolecularly transferred from the bound and activated, optically active hydroperoxide to the ligated sulfoxide in a stereocontrolled manner.

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Identification of MsrA homologues for the preparation of (R)-sulfoxides at high substrate concentrations

Here we report a methionine sulfoxide reductase A (MsrA) homologue with extremely high substrate tolerance and a wide substrate scope for the biocatalytic preparation of enantiopure sulfoxides. This MsrA homologue which was obtained from Pseudomonas alcaliphila (named paMsrA) showed good activity and enantioselectivity towards a series of aryl methyl/ethyl sulfoxides 1a-1k, with electron-withdrawing or electron-donating substituents at the aromatic ring. Chiral sulfoxides in the R configuration were prepared with approximately 50% of yield and up to 99% enantiomeric excess through the asymmetric reductive resolution of racemic sulfoxide catalyzed by the recombinant paMsrA protein. More importantly, kinetic resolution has been successfully accomplished with high enantioselectivity (E > 200) at initial substrate concentrations up to 320 mM (approximately 45 g L-1), which represents a great improvement in the aspect of the substrate concentration for the biocatalytic preparation of chiral sulfoxides.

HPLC enantioseparation on a homochiral MOF-silica composite as a novel chiral stationary phase

The last frontier in the development of chiral stationary phases for chromatographic enantioseparation involves homochiral metal-organic frameworks (MOFs). Using enantiopure (R)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-dicarboxylic acid as a starting material, we prepared three homochiral MOFs that were further used as chiral stationary phases for high-performance liquid chromatography to separate the enantiomers of various kinds of racemic sulfoxides, sec-alcohols, β-lactams, benzoins, flavanones and epoxides. The experimental results showed excellent performances for enantioseparation, and highlighted that enantioseparation on homochiral MOF columns is practical.

Efficient HPLC enantiomer separation using a pillared homochiral metal-organic framework as a novel chiral stationary phase

HPLC enantioseparation of racemates using novel pillared homochiral metal-organic framework-silica composite as chiral stationary phase has been successfully demonstrated.

Enantioselective sulfoxidation reaction catalyzed by a G-quadruplex DNA metalloenzyme

Enantioselective sulfoxidation reaction is achieved for the first time by a DNA metalloenzyme assembled with the human telomeric G-quadruplex DNA and Cu(ii)-4,4′-bimethyl-2,2′-bipyridine complex, and the mixed G-quadruplex architectures are responsible for the catalytic enantioselectivity and activity.

Method for preparing chiral sulfoxide through catalysis of asymmetric oxidation of thioether

The invention provides a method for preparing chiral sulfoxide. According to the method, in a mixed solvent, thioether is used as a substrate, a complex produced by chiral tetradentate organic ligand and a metal manganese compound in situ is used as a cat

Enantioselective oxidation of sulfides with H2O2 catalyzed by a pre-formed manganese complex

A facile and environmentally friendly method is presented for the asymmetric oxidation of sulfides with H2O2, utilizing a pre-formed manganese complex. Just in the presence of a low catalytic amount of carboxylic acid (CA), a variety of sulfide substrates, including aryl alkyl, aryl benzyl and cyclic sulfides, reacted to form chiral sulfoxides in high yields (up to 95%) and excellent enantioselectivities (>99% ee) under mild conditions. Moreover, the practical utility of the method has been demonstrated by the synthesis of esomeprazole and albendazole sulfoxide (ABZO).

Titanium-salan-catalyzed asymmetric sulfoxidations with H2O 2: Design of more versatile catalysts

Titanium-salan complexes with 3,3'-diphenyl substituents in the salicylidene rings of the salan ligand are efficient sulfoxidation catalysts, capable of catalyzing the asymmetric oxidation of bulky aryl benzyl sulfides with H2O2 with good to high enantioselectivities. In this paper, substituent effects on titanium-salan-catalyzed enantioselective oxidation of sulfides to sulfoxides have been systematically investigated. Titanium-salan catalysts with halogen substituents at the 5,5'-positions (3,3'-H2dihydrogen substituted) have been found to catalyze the oxidation of both bulky aryl benzyl sulfides and small alkyl phenyl sulfides with good to high enantioselectivities. Kinetic data witness a direct attack of the sulfide to the electrophilic active oxygen species; a consistent reaction mechanism is proposed. Copyright 2013 John Wiley & Sons, Ltd. Titanium-salan complexes with halogen substituents at the 5,5'-positions are versatile catalysts for the oxidation of both bulky aryl benzyl sulfides and small alkyl phenyl sulfides, demonstrating good to high chemoselectivity (up to 92 %) and enantioselectivity (up to 93 % ee). Copyright

Chiral microporous Ti(salan)-based metal-organic frameworks for asymmetric sulfoxidation

Chiral porous metal-metallosalan frameworks are constructed from an unsymmetrical chiral pyridinecarboxylate ligand derived from Ti(salan) and are shown to be heterogeneous catalysts for asymmetric oxidation of thioethers to sulfoxides.