10119-00-3Relevant articles and documents
Wolff rearrangement of diazo ketones derived from N-p-tolylsulfonyl-protected α- and β-amino acids
Wang, Jianbo,Hou, Yihua
, p. 1919 - 1923 (2007/10/03)
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.