317339-77-8

Upstream product

• 917-54-4 methyllithium 
• 317339-60-9 4-phenylsulfanyl-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridin-2-one 
• 317339-72-3 4-(phenylsulfonyl)-1-tosyl-5,6-dihydro-2-pyridone 
• 70-55-3 toluene-4-sulfonamide 
• 78388-17-7 (E)-N-(but-2-enyl)-4-methylbenzenesulfonamide 
• 64-19-7 acetic acid 
• 10285-80-0 N-tosyl-3-butenylamine 
• 96013-55-7 1-[(4-methylphenyl)sulfonyl]-5,6-dihydro-1H-piperidin-2-one 
• 96013-56-8 4-methyl-1-(toluene-4-sulfonyl)-piperidin-2-one 
• 23438-61-1 1-(toluene-4-sulfonyl)piperidin-2-one 
• 4083-64-1 Tosyl isocyanate 

Relevant academic research and scientific papers

Platinum-Catalyzed Desaturation of Lactams, Ketones, and Lactones

The development of a general platinum-catalyzed desaturation of N-protected lactams, ketones, and lactones to their conjugated α,β-unsaturated counterparts is reported. The reaction operates under mildly acidic conditions at room temperature or 50 °C. It is scalable and tolerates a wide range of functional groups. The complementary reactivity to the palladium-catalyzed desaturation is demonstrated in the efficient conversion of iodide, bromide, and sulfur-containing substrates.

Copper-Catalyzed Desaturation of Lactones, Lactams, and Ketones under pH-Neutral Conditions

A copper-catalyzed desaturation method that is suitable for converting lactones, lactams, and cyclic ketones to their α,β-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium reagents and can be carried out through a simple one-step operation. The protocol uses inexpensive catalysts and reagents and exhibits excellent scalability and functional group tolerance. Notably, tert-butyl alcohol is the only stoichiometric byproduct produced, and overoxidation is not observed. The reaction mechanism has been investigated through control experiments, deuterium labeling, radical clock, electron paramagnetic resonance, high-resolution mass spectrometry, and kinetic studies. The data obtained are consistent with a reaction pathway involving reversible α-deprotonation by a Cu(II)-OtBu species followed by further oxidation of the resulting Cu enolate.

Palladium-Catalyzed Intermolecular Oxidative Cyclization of Allyltosylamides with AcOH: Assembly of 3-Pyrrolin-2-ones

The first example of Pd-catalyzed oxidative cyclization of allyltosylamides with acetic acid is reported. This transformation involved C-N/C-C bond formation and provided 3-pyrrolin-2-ones in a one-pot manner with easy-operation, excellent atom economy and good yields. Mechanistic studies indicate that the reaction proceeds through intermolecular aminopalladation, migratory insertion, reinsertion and β-hydride elimination processes.

Synthesis and applications of tetrahydro-2-pyridinones via aza-Diels - Alder reactions of thio-substituted 1,3-dienes with arylsulfonyl isocyanates

The first aza-Diels - Alder reactions of arylsulfonyl isocyanates with thio-substituted 1,3-dienes via the 3-sulfolene precursors 1 gave the cyclized products 3 with complete control of chemo- and regioselectivity. The cyclized products 3a and 5 underwent further reactions with nucleophiles and bases to give useful heterocyclic compounds. The N-tosyl group of the cyclic products could be selectively replaced by hydrogen or another substituent.

Aza-Diels-Alder reactions and synthetic applications of thio-substituted 1,3-dienes with arylsulfonyl isocyanates

The first aza-Diels-Alder reactions of arylsulfonyl isocyanates with thio-substituted 1,3-dienes via the 3-sulfolene precursors 1 gave the cyclized products 3 with complete control of regio- and chemoselectivity. The cyclized products 3a and 4 underwent further interesting reactions with nucleophiles and bases to give useful heterocyclic compounds. (C) 2000 Elsevier Science Ltd.