52154-24-2

Upstream product

• 934-72-5 Methyl p-tolyl sulfoxide 
• 93-89-0 benzoic acid ethyl ester 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 612-33-9 L-menthyl benzoate 
• 51651-66-2 α-lithiomethyl p-tolyl sulfoxide 
• 83859-18-1 N,N-Dimethyl-N'-[1-phenyl-2-((R)-toluene-4-sulfinyl)-eth-(E)-ylidene]-hydrazine 
• 100-47-0 benzonitrile 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 13466-32-5 acetophenone dimethylhydrazone 
• 33046-45-6 1-phenyl-2-(p-tolylthio)ethanone 
• 97169-19-2 N,N-Dimethyl-N'-[1-phenyl-2-((R)-toluene-4-sulfinyl)-eth-(E)-ylidene]-hydrazine 

Downstream Products

• 52117-57-4 <2S,(S)R>-2-phenyl-1-(4'-methylphenylsulfinyl)-2-propanol 
• 52117-61-0 <2R,(S)R>-2-phenyl-1-(4'-methylphenylsulfinyl)-2-propanol 
• 157660-29-2 (Rs)-3-endo-phenyl-3-exo-(p-tolylsulfinyl)methyl-2,4-dioxa-cis-bicyclo<3.3.0>octane 
• 39201-99-5 (2S,R_S)-1-phenyl-2-p-tolylsulfinylethanol 
• 136457-47-1 (S)-2-hydroxy-2-phenylpropanamide 
• 136347-13-2 (S)-2-hydroxy-3-<(4-methylphenyl)sulfenyl>-2-propanamide 
• 20780-53-4 (R)-Styrene oxide 
• 20780-54-5 (S)-styrene oxide 
• 42330-51-8 rac-(R)-1-phenyl-2-(p-tolylthio)ethan-1-ol 
• 1293384-91-4 (-)-(sR,3R,4S)-5-oxo-3,5-diphenyl-4-p-tolylsulfinyl-pentanal 
• 1293384-94-7 (+)-(sR,1R,2S,3S)-1,3-diphenyl-2-(p-tolylsulfinyl)pentane-1,5-diol 
• 1293384-81-2 (-)-(sR,3S,4S)-5-oxo-3,5-diphenyl-4-p-tolylsulfinyl-pentanal 
• 1293384-90-3 (-)-(sR,3S,4S)-3-methyl-5-oxo-5-phenyl-4-(p-tolylsulfinyl)pentanal 
• 1293384-77-6 (-)-(sR,3R,4S)-3-methyl-5-oxo-5-phenyl-4-(p-tolylsulfinyl)pentanal 

Relevant academic research and scientific papers

The synthesis of chiral β-ketosulfoxides by enantioselective oxidation and their stereocontrolled reduction to β-hydroxysulfoxides

Various chiral non-racemic β-ketosulfoxides, a class of compounds frequently used in asymmetric synthesis, were prepared in good yields by tert-butyl hydroperoxide oxidation of the corresponding sulfides in the presence of a complex between titanium and (

Highly enantiomeric purity conversion of α-sulfinyl oximes and α-sulfinyl hydrazones to the corresponding β-keto sulfoxides with butyltriphenylphosphonium periodate (BUTPPPI)

Butyltriphenylphosphonium periodate (Ph3P+BuIO 4-)1 is readily prepared as a white solid from butyltriphenylphosphonium chloride, performs conversion of α-sulfinyl oximes (2) and α-sulfinyl hydrazones (4) to the

A new and general synthesis of chiral β-ketosulfoxides by reaction of (+)-(R)-methyl p-tolyl sulfoxide with nitriles

The nitrile functional group is efficiently transformed into the β-ketosulfoxide moiety by reaction with the anion formed from (+)-(R)-methyl p-tolyl sulfoxide and aqueous acidic work-up of the reaction.

Bis(1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane) persulfate: A mild and efficient oxidant for cleavage of oxime double bonds under anhydrous conditions

Bis(1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane)persulfate (BAABCPS) 1 readily prepared as orange solid from commercially available 1,4- diazabicyclo[2.2.2]octane (DABCO) and potassium persulfate, converts oximes and α-sulfinyl oximes to the corresponding carbonyl compounds and β-keto sulfoxides respectively, the yields and enantiomeric purity are excellent.

An easy and efficient method for cleavage of carbon-nitrogen double bonds under non-aqueous and neutral conditions

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate (BAABCP) (1), readily prepared as an orange solid from commercially available DABCO (1,4- diazabicyclo [2.2.2]octane, performs oxidation in anhydrous conditions. Under these conditions, the reagent converts phenylhydrazones, p-phenylhydrazones, semicarbazones, and β-keto sulfoxide hydrazones to the corresponding carbonyl compounds and β-keto sulfoxides respectively, the yields and enantioselectivity are excellent.

Alternative approach to the synthesis of optically active β-keto sulfoxides by furylhydroperoxides enantioselective oxidations

Enantiomerically enriched β-keto sulfoxides are obtainable by an alternative method to the classical reaction of the enantiomerically pure α- sulfinyl anion with esters or by Anderson's synthesis, through Sharpless modified kinetic resolution of racemic β-keto sulfoxides. High e.e.s are achieved by combining asymmetric oxidation and kinetic resolution using furylhydroperoxides as oxidants.

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane Periodate: A Mild and Efficient Oxidant for the Cleavage of Oxime Double Bonds under Anhydrous Conditions

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate (BAABCP) (1), readily prepared from commercially available 1,4-diazabicyclo[2.2.2]octane (DABCO) and sodium periodate, converts oximes and α-sulfinyl oximes to the corresponding carbonyl compounds and β-keto sulfoxides, respectively, in high yields and high enantiomeric purity.

Highly Diastereoselective Hydrocyanation of β-Keto Sulfoxides: Synthesis of Enantiomerically Pure Cyanohydrin Derivatives

The reactions of chiral β-keto sulfoxides, R1-CO-CHR2-SOTol (R1 = Me, n-Pr, i-Pr, t-Bu, Ph; R2 = H, Me) with Et2AlCN yield the corresponding sulfinyl cyanohydrins with high yields (85-96percent) and de (>96perce

Intramolecular Stereospecific Pummerer Reactions of Aryl (Substituted-methyl) Sulfoxides Bearing Electron-withdrawing Groups with Acetic Anhydride

The Pummerer reaction of optically active cyanomethyl aryl sulfoxides with acetic anhydride gave the corresponding α-acetoxy sulfides which were induced with a partial asymmetry nearly 30percent at α-carbon, while the 18O-label of the original sulfoxides was retained in more than 85percent in the resulting ester, the Pummerer reaction product.Kinetic experiments with cyanomethyl (p-substituted phenyl) sulfoxides and α,α-dideuterated cyanomethyl p-tolyl sulfoxide in the reaction with acetic anhydride containing a small amount of acetic acid revealed that the rates were correlated with Hammett ?-values and ρ-value of -0.70 was obtained, while the kinetic isotope effect was practically nil, i.e., kH/kD=1.01.These observations indicate clearly that the rearrangement is intramolecular and proceeds via forming a very intimate ion-pair and the rate-determining step is believed to be the S-O bond cleavage after the initial reversible acylation and deprotonation.Elimination of acetic acid proceeds through the Eleb type process.The uneven distribution of 18O in the two oxygens of the resulted ester, i.e., ether and carbonyl oxygens, suggests the recombination of the α-sulfenyl carbonium ion and acetate ion to be very rapid.The pummerer reaction of optically active N,N-dimethyl-p-tolyl-sulfinylacetamide with excess acetic anhydride also gave the corresponding α-acetoxy sulfide in optically active form.In the presence of di-cyclohexylcarbodiimide (DCC), the Pummerer reaction was found to be highly stereoselective affording the corresponding α-acetoxy sulfide with 65percent e.e.Other optically active α-carbonyl-substituted alkyl sulfoxides, i.e., ethyl p-tolylsulfinylacetate and ω-(p-tolylsulfinyl)acetophenone also gave the corresponding highly optically active Pummerer rearrangement products in the treatment with acetic anhydride/DCC system.The Pummerer reaction of the 18O-labeled sulfoxides with acetic anhydride/DCC system gave the corresponding α-acetoxy sulfides which retained much of the original 18O-labels of the sulfoxides.These observations reveal clearly that in the Pummerer reaction of these compounds the acetoxyl migration is intramolecular and takes place through intimate ion-pairs.