102340-68-1

Upstream product

• 67-56-1 methanol 
• 58059-08-8 tert-butyl (R)-p-toluenesulfinylacetate 
• 54930-93-7 (Toluene-4-sulfinyl)-acetic acid methyl ester 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 79-22-1 methyl chloroformate 
• 94404-20-3 (-)-(S_S)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester 

Downstream Products

• 151324-12-8 (1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate 
• 404822-60-2 2-ethyl 4-methyl (-)-(2S,4R,5S,S_S)-2-methyl-5-(2-naphthyl)-4-(p-tolylsulfinyl)pyrrolidine-2,4-dicarboxylate 
• 404822-56-6 2-ethyl 4-methyl (-)-(2S,4R,5R,S_S)-2-methyl-5-(2-naphthyl)-4-(p-tolylsulfinyl)pyrrolidine-2,4-dicarboxylate 
• 404822-59-9 dimethyl (-)-(2S,4S,5S,S_S)-2-methyl-5-(2-naphthyl)-4-(p-tolylsulfinyl)pyrrolidine-2,4-dicarboxylate 
• 404822-55-5 dimethyl (-)-(2S,4S,5R,S_S)-2-methyl-5-(2-naphthyl)-4-(p-tolylsulfinyl)pyrrolidine-2,4-dicarboxylate 
• 404822-58-8 dimethyl (-)-(2S,4R,5S,S_S)-5-(2-naphthyl)-4-(p-tolylsulfinyl)pyrrolidine-2,4-dicarboxylate 
• 404822-54-4 dimethyl (-)-(2S,4S,5R,S_S)-5-(2-naphthyl)-4-(p-tolylsulfinyl)pyrrolidine-2,4-dicarboxylate 
• 404822-57-7 dimethyl (-)-(2S,4R,5S,S_S)-5-phenyl-4-(p-tolylsulfinyl)pyrrolidine-2,4-dicarboxylate 
• 404822-53-3 dimethyl (-)-(2S,4S,5R,S_S)-5-phenyl-4-(p-tolylsulfinyl)pyrrolidine-2,4-dicarboxylate 
• 404822-51-1 methyl (+)-(S)-2-(p-tolylsulfinyl)acrylate 

Relevant academic research and scientific papers

On the applicability of the Jones active site model of pig liver esterase to S-chiral and prochiral sulfinyl substrates

A series of racemic methyl sulfinylacetates was hydrolyzed in the presence of pig liver esterase (PLE) under kinetic resolution conditions to give the corresponding S-chiral sulfinylacetic acids and recovered esters in moderate enantiomeric purity. The Jones active site model was found to be suitable for explaining the enantioselectivity of the above reaction and for the PLE-mediated desymmetrization of prochiral sulfinyldicarboxylates. Copyright (C) 2000 Elsevier Science Ltd.

Asymmetric 1,3-dipolar cycloaddition of N-metalated azomethine ylides to methyl (S)-2-(p-tolylsulfinyl)acrylate. Synthesis of optically pure 2,4,5-trisubstituted 2,5-dihydro-1H-pyrroles

The first 1,3-dipolar reaction of azomethine ylides with optically pure vinyl sulfoxide are reported. The presence of the sulfinyl group increase the reactivity of the acrylate moiety as a dipolarophile, and the reactions evolve with complete regio- and endo-selectivities. Nevertheless, mixtures of the two diastereoisomers 4 and 5 (75-88% de) resulting from the anti dipole/s-cis dipolarophile and syn dipole/s-trans dipolarophile approaches, respectively, are obtained. The stereoselectivity can be controlled by using THF or MeCN as solvents or by changing the reaction temperature in MeCN. After separation of the cycloadducts, optically pure 2,5-dihydro-1H-pyrroles are easily obtained by pyrolytic desulfinylation.

Oxidation of methyl p-tolyl sulfide with backers' yeast: preparation of a synthon of the mevinic acid-type hypocholestemic agents

Bakers' yeast oxidized methyl p-tolyl sulfide to produce the R-sulfoxide 1 in good yield and high enantiomeric excess; the sulfoxide 1 was used to prepare (4R,6S)-tert-butyldimethylsilyloxy-6-hydroxymethyltetrahydropyran-2-one 15.

Bakers' yeast oxidation of methyl para-tolylsulfide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents

The use of (R)-methyl-para-tolylsulfoxide as a chiral auxiliary in a novel synthesis of a key intermediate en route to mevinic acid-type hypocholestemic agents is described. The synthesis is short and simple consisting of eight steps to yield enantiomeric

Studies on chiral organosulfur compounds. III. Lewis acid-catalyzed intramolecular asymmetric pericyclic reactions of chiral α-acetyl and methoxycarbonylvinylic sulfoxides

A chiral α-sulfinyl α,β-unsaturated ketone served as a good chiral diene or enophile in intramolecular Lewis acid-catalyzed asymmetric pericyclic reactions, giving hetero-Diels-Alder reaction products, together with ene reaction products in some cases, in

ENZYME MEDIATED SYNTHESIS OF OPTOCALLY ACTIVE ο-ARENESULFINYLALKANOIC ESTERS

Incubation of methyl arenesulfinylacetates and methyl α-benzenesulfinylpropionate with Corynebacterium equi IFO 3730 afforded the corresponding chiral sulfoxides of high optical purites in moderate to good chemical yields.