Perkin communications. Synthesis of silylated ketenimines from a metallated N-phenyl α-trimethylsilyl imido thioester

Abstract

Lithiated methyl N-phenyl-2-trimethylsilylethanimidothioate is regioselectively C-alkylated at –78 °C but, at a higher temperature in the presence of 1 equiv. of butyllithium, it is converted into a lithiated ketenimine which can be protonated or alkylated to give new and stable silylated ketenimines