22456-89-9

Upstream product

• 13307-61-4 Isobutylthiobenzene 
• 108-98-5 thiophenol 
• 100-59-4 phenylmagnesium chloride 
• 939962-74-0 bis(2,2’-bromophenyl) sulfoxide 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 2892-94-6 di-iso-butylmagnesium 
• 7601-90-3 perchloric acid 
• 64-17-5 ethanol 
• 7722-84-1 dihydrogen peroxide 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 13640-71-6 2-methyl-1-(phenylthio)-1-propene 
• 64732-74-7 (1-Isopropyl-but-3-enylsulfanyl)-benzene 
• 13307-61-4 Isobutylthiobenzene 
• 67833-43-6 1-chloro-2-methylpropyl phenyl sulfoxide 
• 22456-89-9 (R)-(+)-isobutyl phenyl sulfoxide 
• 22456-89-9 (S)-(-)-isobutyl phenyl sulfoxide 
• 98711-79-6 2-methyl-6-(p-tolyl)-3-phenylsulphinylheptan-4-one 
• 778-24-5 Dimethyldiphenylsilane 
• 129315-31-7 tert.-Butyl (2S*,3S*)-2,4-dimethyl-3-(phenylthio)thiopentanoate and tert.-Butyl (2R*,3S*)-2,4-dimethyl-3-(phenylthio)thiopentanoate 
• 129315-20-4 2,2,6-Trimethyl-5-phenylsulfanyl-heptan-3-one 

Relevant academic research and scientific papers

Prochiral Diheteroaryl Sulfoxides and Their Reactions with (S)-Li2-BINOLate-Activated Diisobutylmagnesium

5-Membered ring heterocycles were α-lithiated or α-magnesiated so that they attacked SOCl2 or SO(OMe)2 forming symmetric – i.e. prochiral – diheteroaryl sulfoxides. The latter were treated with a 0.5- or 1.2-fold molar amount of 5:4 mixtures of dilithium (S)-BINOLate and diisobutylmagnesium. This allowed five asymmetric sulfoxide/magnesium exchange reactions to occur. They delivered asymmetric sulfoxides in up to 77 % yield and with up to 88 % ee. Surprisingly, four related diheteroaryl sulfoxides, bis(2-pyridyl) sulfoxide, and bis(3-pyridyl) sulfoxide were unamenable to such exchanges and decomposed instead.

Chiral: N, N ′-dioxide-iron(iii)-catalyzed asymmetric sulfoxidation with hydrogen peroxide

A highly enantioselective sulfoxidation of various sulfides has been achieved by a N,N′-dioxide-iron(iii) complex with 35% aq. H2O2 as the oxidant. The utility of the current method was demonstrated by asymmetric gram-scale synthesis of drug molecule (R)-modafinil. Moreover, a possible working mode was provided to elucidate the chiral induction.

Design, synthesis and antiplasmodial evaluation of sulfoximine-triazole hybrids as potential antimalarial prototypes

Background: Malaria, caused by the deadly Plasmodium falciparum strain, claims the lives of millions of people annually. The emergence of drug-resistant strains of P. falciparum to the artemisinin-based combination therapy (ACT), the last line of defense against malaria, is worrisome and urges for the development of new chemo-types with a new mode of action. In the search of new antimalarial agents, hybrids of triazoles and other known antimalarial drugs have been reported to possess better activity than either of the parent compounds administered individually. Despite their better activity, no hybrid antimalarial drugs have been developed so far. Objective: In the hope of developing new antimalarial prototypes, we propose the design, synthesis and antimalarial evaluation of novel sulfoximine-triazole hybrids owing to their interesting biological and physiological properties. Method: The sulfoximine part of the hybrid will be synthesized via imidation of the corresponding sulfoxide. Propargylation of the NH moiety of the sulfoximine followed by copper-catalyzed click chemistry with benzyl azide was envisaged to provide the target sulfoximine-triazole hybrids. Results: Five novel sulfoximine-triazole hybrids possessing various substituents on the sulfoximine moiety have been successfully synthesized and evaluated for their antiplasmodial and cytotoxicity activities. The results revealed that the co-presence of the sulfoximine and triazole moieties along with a lipophilic alkyl substituent on the sulfur atom impart significant activity. Conclusion: Sulfoximine-triazole hybrids could be used as a prototype for the synthesis of new derivatives with better antiplasmodial activities.

Symmetric diarylsulfoxides as asymmetric sulfinylating reagents for dialkylmagnesium compounds

At -78 °C, primary dialkylmagnesium compounds reacted with diarylsulfoxides when 1.5 equiv of the dilithium salt of (S)-BINOL was added as a promotor. Alkyl aryl sulfoxides resulted in up to quantitative yield and with up to 97% ee. This demonstrates the feasibility of asymmetric sulfinylations by achiral sulfinylating agents (from the perspective of Alkyl2Mg) as well as the feasibility of asymmetric sulfoxide-magnesium exchanges (from the perspective of Ar2SO).

Diastereoconvergent synthesis of trans -5-hydroxy-6-substituted-2- piperidinones by addition-cyclization-deprotection process

A diastereoselective one-pot approach to access trans-5-hydroxy-6- substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by α-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.

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.

Copper-catalyzed asymmetric oxidation of sulfides

Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of th

Enantioselective inclusion of chiral alkyl aryl sulfoxides in a supramolecular helical channel consisting of an enantiopure 1,2-amino alcohol and an achiral carboxylic acid

The enantioselective clathrate formation of alkyl aryl sulfoxides 4 was achieved with dissymmetric one-dimensional helical channels created in two-component hosts consisting of (1R,2S)-2-amino-1,2-diphenylethanol 1 and an achiral carboxylic acid, p-tert-butylbenzoic acid 2, or 2-anthraquinonecarboxylic acid 3. X-ray crystallographic analyses showed that the host framework (1R,2S)-1·3 in the single crystal of a clathrate with methyl p-methylphenyl sulfoxide 4n [(1R,2S)-1·3·4n (single)] maintained a supramolecular helical array as those of the solvent-included single crystals (1R,2S)-1·3·EtOH(single) and (1R,2S)-1·3·H2O·THF(single), while the guest 4n molecules were highly disordered. Moreover, the X-ray powder diffraction pattern of (1R,2S)-1·3·4n(clathrate) obtained through the clathrate formation demonstrated that the molecular arrangements of (1R,2S)-1, 3, and 4n were not the same as those which appeared in (1R,2S)-1·3·4n(single); the channel was enlarged. These results are consistently explained by assuming the dynamic motion of the framework (1R,2S)-1·3 to achieve widely applicable clathrate formation.

Diastereoselective radical alkylations of alkyl aryl sulfoxides

1,2-Asymmetric induction in reactions of arylsulfinylated radicals has been examined and compared to the anionic processes. A rule of thumb allowing to predict the stereoselectivity is presented.

Asymmetric Oxidation of Alkyl Aryl Sulfides in Crystalline Cyclodextrin Complexes

Alkyl aryl sulfides were enantioselectively oxidized in the crystalline cyclodextrin (CD) complexes under various conditions.The oxidation of alkyl phenyl sulfoxides in the β-cyclodextrin (β-CD) complexes resulted in higher chiral induction than that in t