Photorearrangement of N-alkanoyl β-enaminones. Application to the synthesis of α-amino-β,γ-unsaturated acid derivatives

Article abstract of DOI:10.1016/0040-4020(95)01090-4

The irradiation of N-alkanoyll-β-enaminones lead to the formation of spiranic β-lactams which undergo C-N bond cleavage during chromatography on alumina giving cycloalkenones functionalized at position 3. This new rearrangement has been applied to the synthesis of α-amino-β,γ-unsaturated amides in one step and gives convenient yields.