In the first key step, the chirality of the 𝛼-chiral allylic amine is transferred from C𝛼-to C𝛾-position by the TBD organocatalyst in a stepwise manner, through the formation of a tight-ion-pair intermediate with induced noncovalent chirality. A mixture of imine and enamine intermediates were formed, which upon reduction afforded α,γ-chiral trifluoromethylated amines, however only moderate diastereoselectivity was obtained. Herein, we report the selective trapping the enamine-tautomer after the stereospecific isomerization through subsequent acid chloride addition in a one-pot two steps procedure to synthesize 𝛾-chiral, trifluoromethylated secondary enamides, which can be further transformed into various chiral complex scaffolds (Scheme 2C). As the optimal conditions for the stereospecific isomerization of 𝛼-chiral allylic amines have been previously established, we started our investigation by optimizing the parameters for the one-pot two steps synthesis of the 𝛾-chiral enamides by adding BzCl and Et3N after the isomerization. Firstly, the amount of BzCl was examined and we observed that 2.0 equiv. of BzCl were necessary to obtain the desired product in high yields (Table , entry 1-3). Then, we optimized the equivalents of Et3N (Table , entry 4). Lowering the temperature to 20 °C had drastic effect on the yield of the reaction (Table , entry 5). Further evaluation of other organic bases demonstrated that DABCO was the most efficient base for this step (Table , entry 6-8). Attempts to lower the amount of DABCO only led to a decreased in yield (Table , entry 9).