173034-72-5

Upstream product

• 43188-65-4 methyl (2S,3S)-3-methyl-1-[(4-methylphenyl)sulfonyl]aziridne-2-carboxylate 
• 67-56-1 methanol 
• 31981-99-4 N-((S)-3-Diazo-1-methyl-2-oxo-propyl)-4-methyl-benzenesulfonamide 
• 814256-29-6 (S_S,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-aminobutanoate 
• 4816-81-3 p-tosyl-L-alanine 
• 56271-34-2 (S)-2-(4-methylbenzenesulfonylamino)propionyl chloride 
• 43188-53-0 (2S,3R)-methyl-N-(4-methylphenylsulfonyl)-3-hydroxy-2-aminobutanoate 
• 1217800-94-6 C₁₄H₁₉NO₃S 

Downstream Products

• 209850-49-7 (S)-3-(Toluene-4-sulfonylamino)-butyric acid 
• 883458-39-7 (S)-(-)-4-methyl-N-(4-oxobutan-2-yl)benzenesulfonamide 
• 209850-56-6 N-((S)-4-Diazo-1-methyl-3-oxo-butyl)-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

Addition of lithiated methoxyallene to aziridines - A novel access to enantiopure piperidine and β-amino acid derivatives

Addition of lithiated methoxyallene to aziridine derivatives provided the expected primary addition products. The less substituted carbon of the aziridine ring was attacked selectively. The primary adducts could be converted to enantiopure piperidine deri

Asymmetric synthesis of trans-2,5-disubstituted pyrrolidines from enantiopure homoallylic amines. Synthesis of pyrrolidine (-)-197B

Iodocyclization of sulfinimine-derived enantiopure homoallylic sulfonamides affords trans-2,5-disubstituted 3-iodopyrrolidines and represents valuable methodology for the asymmetric synthesis of this important heterocyclic ring system.

Wolff rearrangement of diazo ketones derived from N-p-tolylsulfonyl-protected α- and β-amino acids

Diazo ketones derived from N-p-tolylsulfonyl (tosyl)-protected α- and β-amino acids have been synthesized and their diazo decomposition under standard Wolff rearrangement conditions, PhCO2Ag-Et3N-MeOH, has been investigated. It is observed that, under these conditions, several different reaction pathways, including direct carbene N-H insertion, are possible. The reaction is markedly affected by the N-protecting group, the substrate structure and solvent. For those diazo ketones derived from N-tosyl-protected β-amino acids, the diazo decomposition with anhydrous THF as solvent and PhCO2Ag dissolved in Et3N as catalyst gives the corresponding 5-substituted pyrrolidinones in excellent yields.

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.

Regiospecific reductive ring cleavage of N-substituted aziridine-2-carboxylates and An aziridine-2-methanol via catalytic hydrogenation using Pd as a catalyst

Regiospecific reductive ring cleavage was accomplished in the reaction of N-α-methylbenzyl substituted aziridine-2-carboxylate and aziridine-2-methanol under a catalytic hydrogenation condition. The regiospecificity was determined by the substituent at C-