Results and Discussion

Abstract

We envisioned a chemoselective nucleophilic functionalisation of amides through Umpolung. A challenge that could arise are the different electrophilic centres on the enolonium ion V itself. Attack on the α-carbon would lead to the desired product, while the addition of the nucleophile at carbon 4 of the lutidinium moiety would lead to a functionalised lutidine with concomitant release of the starting (Figure 13).