82125-95-9

Upstream product

• 32065-38-6 N-(4-diazo-3-oxo-butyl)-toluene-4-sulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 78388-17-7 (E)-N-(but-2-enyl)-4-methylbenzenesulfonamide 
• 78388-17-7 N-(p-toluenesulfonyl)but-2-en-1-amine 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 
• 172265-18-8 1-{1-[(4-methylphenyl)sulfonyl]aziridin-2-yl}ethanone 
• 100-52-7 benzaldehyde 
• 78-94-4 methyl vinyl ketone 
• 82125-94-8 C₁₂H₁₅NO₅S 
• 676-58-4 methylmagnesium chloride 
• 127700-57-6 1-p-toluensulfonylaziridine-(2S)-carboxylic acid tert-butyl ester 
• 917-54-4 methyllithium 

Downstream Products

• 95484-04-1 N-{3-[2-(3,4-Dihydroxy-phenyl)-2-hydroxy-ethylamino]-butyl}-4-methyl-benzenesulfonamide 
• 3634-89-7 N-(p-toluenesulfonyl)aziridine 

Relevant academic research and scientific papers

A Domino Aza-Prins/Friedel-Crafts Reaction for the Synthesis of Benzomorphans

A new domino sequence involving an aza-Prins cyclization and a Friedel-Crafts reaction is reported. The starting materials are N-tosylimines prepared in situ from N-tosylated homoallylamines and derivatives of phenylacetaldehyde. The domino reactions are

Regioselective Wacker-Type Oxidation of Internal Olefins in tBuOH Using Oxygen as the Sole Oxidant and tBuONO as the Organic Redox Cocatalyst

A regioselective Wacker-Tsuji oxidation of internal olefins in tBuOH has been developed using oxygen as the terminal oxidant and tert-butyl nitrite as the simple organic redox cocatalyst without the involvement of hazardous cocatalysts or harsh reaction conditions. A series of internal olefins bearing various functional groups can be oxidized to the corresponding substituted ketones in generally good yields with high regioselectivities.

PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES

The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.

Regioselective Wacker oxidation of internal alkenes: Rapid access to functionalized ketones facilitated by cross-metathesis

Wacka wacka: The title reaction makes use of a wide range of directing groups (DG) to enable the highly regioselective oxidation of alkenes, and occurs predictably at the distal position. Both E and Z alkenes afford valuable functionalized ketones and cross-metathesis was shown to facilitate the preparation of the starting materials. BQ=benzoquinone. Copyright

Selective reduction of acyl aziridines to Mannich bases using silyllithium reagents

Mannich bases are prepared from the selective α-reduction of acyl aziridines using silyllithium reagents. The reaction proceeds via an aziridine ring-opening assisted Brook rearrangement.

Titanium tetraiodide mediated reductive opening of aziridines, leading to the aldol and mannich-type reactions

Reductive ring-opening of N-tosylazirindes was readily carried out with titanium tetraiodide to form the titanium enolates, which in turn were subjected to addition reaction with aldehydes or imines to give aldol or Mannich-type products in good yields.

DABCO-catalyzed reactions of hydrazones with activated olefins

This paper describes several highly efficient DABCO-catalyzed aza-Michael addition reactions of hydrazones to activated olefins. In most cases, these aza-Michael addition reactions gave the corresponding products in high yields under mild conditions. The plausible reaction mechanism is discussed on the basis of deuterium labeling experiments. Upon treatment with HCl, the corresponding cyclized products can be obtained in high yields from the Michael addition products.

Diazo decomposition in the presence of tributyltin hydride. Reduction of α-diazo carbonyl compounds

The diazo group of a series of α-diazo carbonyl compounds can be reduced to the corresponding CH2 group by Bu3SnH under Cu(acac)2-catalytic or photochemical conditions. The mechanistic aspects of this reaction were investigated in some detail, and a possible reaction pathway was discussed. (C) 2000 Elsevier Science Ltd.

Reduction of 2-acylaziridines by samarium(II) iodide. An efficient and regioselective route to β-amino carbonyl compounds

A convenient method for the reduction of 2-acylaziridines, aziridine-2- carboxylates and aziridine-2-carboxamides is described. The reduction of all of the substrates examined was extremely rapid and highly regioselective, giving rise to β-amino carbonyl compounds. This method appears to be general for all of the classes of aziridines mentioned above, and also tolerates a variety of nitrogen protecting groups.