52960-60-8

Upstream product

• 774-48-1 (diethoxymethyl)benzene 
• 1129-26-6 4-methoxybenzene sulfonamide 
• 64705-26-6 (2S,3S)-2-(4-Methoxy-benzenesulfonyl)-3-phenyl-oxaziridine 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-52-7 benzaldehyde 
• 13909-34-7 N-benzylidenephenylsulfonamide 
• 119059-70-0 N-benzyl-4-methoxybenzenesulfonamide 
• 108-88-3 toluene 

Downstream Products

• 64705-26-6 cis-2-(4-methoxy-benzenesulfonyl)-3-phenyl-oxaziridine 
• 64705-26-6 (2S,3S)-2-(4-Methoxy-benzenesulfonyl)-3-phenyl-oxaziridine 
• 1056904-12-1 naphthalen-2-yl (S)-2-((4-Methoxyphenylsulfonamido)(phenylmethyl))acrylate 
• 1087163-86-7 C₂₄H₂₄N₂O₅S 
• 1087163-76-5 C₂₄H₂₄N₂O₅S 
• 645-49-8 cis-stilben 
• 1885-38-7 cinnamic nitrile 
• 24840-05-9 (Z)-cinnamonitrile 
• 4192-77-2 ethyl cinnamate 
• 1285665-46-4 C₂₅H₂₂N₂O₃S 
• 1294493-94-9 C₂₈H₂₃N₂O₂P 
• 1294493-77-8 2-methylene-4-nitro-3-phenylbutanenitrile 
• 38101-69-8 2-[(E)-styryl]quinoline 
• 1356390-93-6 4-methoxy-N-(2,2,2-trifluoro-1-phenylethyl)benzenesulfonamide 

Relevant academic research and scientific papers

Practical N-hydroxyphthalimide-mediated oxidation of sulfonamides to N-sulfonylimines

A new method to prepare sulfonylimines through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in

Sulfinate-Organocatalyzed (3+2) Annulation Reaction of Propargyl or Allenyl Sulfones with Activated Imines

An operationally simple methodology for the synthesis of 4-sulfonyl-3-pyrrolines is described using a propargylic sulfone and N-sulfonyl imines as substrates. This annulation process is initiated by an arenesulfinate organocatalyst, which allows a smooth isomerization of the alkynyl precursor into the corresponding allene, followed by the generation of a highly reactive allyl sulfone anion. An asymmetric version involving an unprecedented enantiopure sulfinate–ammonium cooperative ion pair (PhSO2– R4N+*) was investigated. A proof-of-concept, with enantiomeric excesses of up to 41 %, was obtained according to a preliminary screening of commercially available chiral phase-transfer catalysts.

Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction

A simple and efficient synthetic route to substituted N-sulfinyl and N-sulfonyl azetidines is described involving imino-aldol reaction of ester enolates with racemic and non-racemic aldimines for obtaining β-amino esters as a key step. These β-amino ester

Probing the Diastereoselectivity of Staudinger Reactions Catalyzed by N-Heterocyclic Carbenes

The reaction of ethylphenylketene with 1,3-dimesitylimidazol-2-ylidene (IMes) or 1,3-dimesitylimidazolin-2-ylidene (SIMes) afforded the corresponding azolium enolates in high yields. The two zwitterions were fully characterized by various analytical techn

Organocatalytic trifluoromethylation of imines using phase-transfer catalysis with phenoxides. A general platform for catalytic additions of organosilanes to imines

A new approach to additions of silicon nucleophiles to imines was developed. The method is based on the phase-transfer of phenoxides by ammonium catalysts, overcoming the inability of amide adducts in promoting the reactions.

Oxidative imination of toluenes catalyzed by Pd-Au/silica gel under mild reaction conditions

A Pd-Au/SiO2 catalyst was prepared for the oxidative imination of toluenes with up to 99% yields in the absence of dehydrating agents under mild conditions. Nanoparticles with a PdO layer and PdO-Au core may be the active structure for the reaction.

A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines

The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph3PCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly by replacing the aldehydes used in the Wittig reaction with N-sulfonyl imines, which possess distinct electronic and steric properties relative to aldehydes. A broad range of aromatic, α,β-unsaturated, and aliphatic imines bearing appropriate N-sulfonyl groups smoothly undergo olefination reaction with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity. Moreover, this tunable protocol has been successfully applied to the highly stereoselective synthesis of two anticancer agents, DMU-212 and its Z-isomer.

NEW DIOXOMORPHOLINES FOR COMBATING ENDOPARASITES

The present invention relates to new dioxomorpholines, to their use for combating endoparasites and to processes for their preparation.

α-Amino acids and N-protected α-amino aldehydes by stereoselective additions of a chiral vinyllithium reagent to sulfonylimines

The chiral vinyllithium reagent (S)-1b, readily generated from dibromoalkene (S)-1a by bromine/lithium exchange, adds stereoselectively to mesitylsulfonylimines 2a-f so that the diastereomers 3 are obtained in ≥98% d.e. after column chromatography. The bromoalkenes 3a-d are submitted to ozonolysis in methanol to give α-mesitylsulfonylamino esters (S)-8a-d which can be hydrolyzed to deliver N-protected α- amino acids in >95% e.e. On the other hand, α-mesitylsulfonylamino aldehydes 12a-d are available when bromoalkenes 3a, d-f are first debrominated (→ 11a-d) and subsequently ozonized. In order to avoid reacemization, the aldehydes 12a-d are not purified but submitted to a Mukaiyama-type aldol addition whereby hydroxyesters 15a-d are formed as single diastereomers in a chelate-controlled reaction. The relative configuration of the esters 15a-d is proven by conversion into the oxazolidinones 16a-d whose optical purity is determined to exceed 92% e.e. by 1H-NMR measurements in the presence of chiral shift reagents. The sulfonylimine 21a and a series of para-substituted derivatives 21b-h are also allowed to react with the vinyllithium reagent 1b to give mixtures of diastereomers 22/23. The logarithms of the diastereomeric ratios 22:23 correlate with Hammett's σ-values. VCH Verlagsgesellschaft mbH, 1997.

HAMMETT INVESTIGATION OF IODIDE-ION-INDUCED DEOXYGENATIVE REDUCTION OF 2-ARYL'SULPHONYL-3 ARYLOXAZIRIDINES IN METHANOL-WATER (50percent v/v)

The Hammett substituent dependence of the iodide ion induced deoxygenation of 2-aryl'sulphonyl-3-aryloxaziridines, in aqu. methanol suggests that the reaction proceeds by nucleophilic attack on oxygen with concomitant O-N bond breakage.