α-Nitrogenated organolithium compounds from N-(tosylmethyl)amides

Article abstract of DOI:10.1055/s-1997-6111

Deprotonation of α-amido sulfones 7 with BuⁿLi at -90°C followed by reaction with electrophiles leads, depending on the substitution on the amidic nitrogen to enamides 10 (secondary amides 7a,b) or functionalised α-amido sulfones 12 (tertiary amides 7c,d). Naphthalene-catalysed lithiation of tertiary α-amido sulfones 7c,d in the presence of electrophiles (Barbier conditions) at -78°C affords functionalised amides 13.