On the interaction of silyl triflates with enamines: iminium ion formation versus silylation

The interaction of Me3SiOTf and (C6F5)3SiOTf with enamines generating α-silyl-substituted iminium ions is investigated. A trimethylsilyl iminium cation is formed as a long-lived species observable by NMR spectroscopy, whilst the tris(pentafluorophenyl)silyl analogue is very labile and prone to the loss of a proton. On the basis of the latter phenomenon, a method for the synthesis of β-silyl enamines is proposed.

The interaction of silyl triflates with enamines has been studied.Figure optionsDownload as PowerPoint slide