Having optimized the reaction conditions for the stereospecific isomerization (Table , entry 11), we went on to study the reduction of the enamine intermediate to form ,chiral trifluoromethylated aliphatic amine 6a (Table ). Compound rac-4a was subjected to the isomerization conditions as before, followed by treatment with a reducing agent in a two-step one-pot protocol. When the isomerization was completed, the temperature was adjusted before addition of the reductant. No further manipulations were done. When NaBH4 was used at room temperature, good yields were obtained but the diastereoselectivity was poor (Table , entry 1). DIBAL-H showed moderate diastereoselectivity in favor of