209850-49-7

Upstream product

• 4816-81-3 p-tosyl-L-alanine 
• 31981-99-4 N-((S)-3-Diazo-1-methyl-2-oxo-propyl)-4-methyl-benzenesulfonamide 
• 56271-34-2 (S)-2-(4-methylbenzenesulfonylamino)propionyl chloride 
• 100132-60-3 (S)-2-(toluene-4-sulfonamido)propan-1-ol 
• 875438-78-1 (3S)-(p-toluenesulfonyl)amino-butyronitrile 
• 173034-72-5 methyl (3S)-3-(4-methylbenzene-1-sulfonamido)butanoate 

Downstream Products

• 209850-56-6 N-((S)-4-Diazo-1-methyl-3-oxo-butyl)-4-methyl-benzenesulfonamide 
• 936012-08-7 N-(3-hydroxy-1-methyl-propyl)-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

A convenient synthetic route to enantiopure N-tosylazetidines from α-amino acids

A general and convenient synthetic route to various chiral 2-substituted- and 2,4-disubstituted-N-tosylazetidines (ee >99%) is described in good overall yields starting from chiral α-amino acids using very simple chemistry.

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.