20288-49-7

Upstream product

• 1517-82-4 (-)-(S)-O-menthyl p-toluenesulfinate 
• 109-65-9 1-bromo-butane 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 21784-96-3 n-butyl 4-methylphenyl sulfide 
• 61187-72-2 (R)-(1-Butenyl)-p-tolyl-sulfoxid 
• 693-04-9 butyl magnesium bromide 
• 190448-84-1 (1S,5R,7R)-10,10-Dimethyl-4-((R)-toluene-4-sulfinyl)-3-thia-4-aza-tricyclo[5.2.1.0^1,5]decane 3,3-dioxide 
• 63268-43-9 (+)-(S)-dimethyl-p-tolylsulfinylmethanephosphonate 
• 1774-35-2 di(p-tolyl) sulfoxide 
• 1191-47-5 dibutylmagnesium 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 693-03-8 n-butyl magnesium bromide 
• 144539-55-9 (+)-(S)-1-bromovinyl-p-tolyl sulfoxide 
• 30506-35-5 butyl(p-tolyl)sulfoxide 

Downstream Products

• 51774-53-9 n-Butyl-p-tolylsulfoximin 
• 100907-33-3 (R)-2-Methylene-4-((R)-toluene-4-sulfinyl)-heptanoic acid 
• 100907-23-1 (S)-2-Methylene-4-((R)-toluene-4-sulfinyl)-heptanoic acid 
• 879881-79-5 (R)-5-Chloro-5-(toluene-4-sulfonyl)-octan-4-one 
• 879881-77-3 (R)-5-Chloro-5-(toluene-4-sulfonyl)-octan-4-ol 
• 879881-82-0 (S)-2-Ethyl-3-(toluene-4-sulfonyl)-hexanoic acid benzylamide 
• 100907-27-5 (S)-2-Methylene-4-p-tolylsulfanyl-heptanoic acid 

Relevant academic research and scientific papers

Development of a simple high-throughput assay for directed evolution of enantioselective sulfoxide reductases

We report on the development of high-throughput fluorogenic assay that can streamline directed evolution of enantioselective sulfoxide reductases. As a model, methionine sulfoxide reductase A (MsrA) has been evolved to expand its limited substrate scope. The resulting mutant MsrA can resolve a range of new challenging racemic sulfoxides with high efficiency including the pharmaceutically relevant albendazole sulfoxide. The simplicity and the level of throughput make this method also suitable for the screening of metagenomic libraries in future for the discovery of new enzymes with similar reactivities.

Chiral Br?nsted-Acid-Catalyzed Asymmetric Oxidation of Sulfenamide by Using H2O2: A Versatile Access to Sulfinamide and Sulfoxide with High Enantioselectivity

Herein, we describe an example of catalytic asymmetric synthesis of sulfinamides. Aromatic sulfenamides were chosen as useful substrates, because of the indispensable N-H bond, which could form an efficient hydrogen bond with chiral phosphoric acid. Hsub

Method for catalyzing asymmetric oxidation of sulfur ether

The invention provides a method for asymmetrically oxidizing sulfur ether. The sulfur ether is subjected to asymmetric catalytic oxidation reaction by taking a chiral complex formed by a four-tooth nitrogen organic ligand and a metal scandium compound as a catalyst and taking hydrogen peroxide as an oxidizing agent to obtain a corresponding chiral sulfoxide compound, and the yield and the enantioselectivity are more than 90 percent. The reaction has the advantages of cleanness, mild reaction condition, high conversion rate and high enantioselectivity. The method has an industrial prospect.

Intermolecular Pummerer Coupling with Carbon Nucleophiles in Non-Electrophilic Media

A new Pummerer-type C?C coupling protocol is introduced based on turbo-organomagnesium amides, which unlike traditional Pummerer reactions, does not require strong electrophilic activators, engages a broad range of C(sp3)-, C(sp2)-, and C(sp)-nucleophiles, and seamlessly integrates with C?H and C?X magnesiation. Given the central character of sulfur compounds in organic chemistry, this protocol allows access to unrelated carbonyls, olefins, organometallics, halides, and boronic esters through a single strategy.

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).

Asymmetric oxidation catalysis by a porphyrin-inspired manganese complex: Highly enantioselective sulfoxidation with a wide substrate scope

The first genuinely promising porphyrin-inspired manganese-catalyzed asymmetric sulfoxidation method using hydrogen peroxide has been successfully developed, allowing for rapidly oxidizing (0.5-1.0 h) a wide variety of sulfides in high yields with excellent enantioselectivities (up to >99% ee).

Application of a novel 1,3-diol with a benzyl backbone as chiral ligand for asymmetric oxidation of sulfides to sulfoxides

A chiral 1,3-diol with a benzyl backbone has been used for the asymmetric oxidation of sulfides to sulfoxides. Moderate to good yields and enantioselectivity (upto 87% ee) have been observed.

Conjugate additions to alkylidene bis(sulfoxides)

A general study on the conjugate addition of anionic nucleophiles to alkylidene bis(sulfoxides) is presented. Alkoxides gave high yielding and diastereoselective addition reactions, which could be influenced by solvents and the counteranion. Azides provided an interesting entry into sulfinyl-substituted triazoles. Organometallics, mainly copper reagents, proved also to be valuable nucleophiles, and complete inversion of the stereoselectivity was achieved in the addition reaction with the latter. Modelizations provide a rationale for the observed diastereoselectivity. Taking the Michael: Alkylidene bis(sulfoxides) are exquisite Michael acceptors toward a broad series of nucleophiles, and in most cases the reaction affords the adducts in high yields with complete diastereoselectivity.

Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)- arylsulfinamides

A novel and simple process for the preparation of enantiomerically pure (SS)-benzenesulfinamide (SS)-3a, (SS)-p- toluenesulfinamide (SS)-3b, (SS)-p-chloro- benzenesulfinamide (SS)-3c and (SS)-p- fluorobenzenesulfinamide (SS)-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)- arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,SS)-N-benzyl-N-(1-phenylethyl)- arylsulfinamides (R,SS)-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,SS)-1 were then converted into four enantiopure (RS)-methyl arylsulfinates (RS)-2, and finally into four enantiopure (SS)- arylsulfinamides (SS)-3 in good yields.

Novel synthesis of optically active 2-ethylhexanoic acid, 2-ethylhexanol, and 2-ethylhexylamine via the asymmetric favorskii rearrangement

The asymmetric Favorskii rearrangement of optically active α-haloketones, which are easily prepared from chiral menthyl-4- toluenesulfoxide in several steps using primary or secondary amines, yields their corresponding secondary or tertiary chiral amides.