Highly diastereoselective synthesis of optically pure trifluoromethyl-substituted imidazolidine, oxazolidine and thiazolidine

Optically pure trifluoromethylated imidazolidine, oxazolidine, and thiazolidine derivatives were synthesized through double Michael addition of chiral amino amides, amino acids, or amino alcohols to an easily available trifluoromethyl building block methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate. These reactions occurred highly diastereo-selectively (up to 99:1) in good yields (65–96%) under mild conditions.