2-Aza-1, 3-dienes bearing an activating trialkylsilyloxy group at C-3 have been prepared via three routes. The first route involves the silylation of N-acylimidates which are readily available from iminoether hydrochlorides and acid chlorides. According to a more general route towards these doubly activated dienes, N-trialkylsilylimidates and N-trialkylsilylimines derived from non-enolizable aldehydes were conveniently converted in a one-pot ...