Simple access to novel β-hydroxy-β-trifluoromethyl imines

Selected imines reacted with three different trifluoromethyl group-containing ketones in a non-catalyzed manner at ambient temperature to give the corresponding β-hydroxy-β-trifluoromethyl imines in good to excellent yields. With 1,1,1-trifluoroacetone a 1:1 and a 2:1 reaction product was obtained. The reduction of 2-isopropylimino-4-phenyl-5,5,5-trifluoropentan-4-ol led to a 5:1 diastereomeric mixture of the corresponding amine, whose dominant form was found to be (2S, 4R) 4-isopropylamino-4-phenyl-2-trifluoromethyl-butan-2-ol in the solid state. Hydrolysis in one case gave the respective β-hydroxy ketone.