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

Abstract

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.

References

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