New strategies for the synthesis of fluorinated vinylogous amidines and beta-enamino ketones

Reaction of fluorinated imidoyl chlorides 3 with ketimines 1a provides fluo rinated 1,3-diimines, which were exclusively isolated as vinylogous amidine tautomers 2 beta, with good yields. Fluorinated beta-enamino ketones 4 are obtained by regioselective hydrolysis of 2. Complementary methods for the synthesis of regioisomeric beta-enamino ketones 4 and 5 are also reported. These methods include the reaction of azaenolates of ketimines with fluorin ated esters 6 and reactions of ketone enolates with fluorinated imidoyl chl orides 3. The behavior of these systems in hydrolysis reactions was also te sted.