Diastereoselective synthesis of cyclic 1,3-aminoalcohols bearing CF3(CCl3)-groups

An aldol-type reaction of cyclic imines and cyclic lactims with carbonyl compounds activated by electron withdrawing trifluoromethyl or trichloromethyl groups proceeded without any catalyst under mild condition. β-Hydroxymethyl substituted cyclic imines or imidates are formed as a result of the reaction. The reduction of the prepared imines leads stereoselectively to the cyclic 1,3-aminoalcohols. Application of methyl trifluoropyruvate in this transformation opens an opportunity for the synthesis of γ-aminoacids derivatives which contain pyrrolidine moiety.

Graphical abstractReaction of cyclic imines and lactims with trifluoromethyl or trichloromethylcarbonyl compounds proceeded without any catalyst. The reduction of the prepared products leads stereoselectively to the 1,3-aminoalcohols containing pyrrolidine moiety.Figure optionsDownload full-size imageDownload as PowerPoint slide