Enantioselective Synthesis of Thiazole-Derived α-Perfluoroalkylated 5–7-Membered Amines

Enantioselective synthesis of thiazole-containing alpha-perfluoroalkylated cyclic amines was elaborated. Organocatalytic Strecker reaction with 5-7 membered cyclic ketimines was used as a key step of sequence. The prepared chiral amino nitriles bearing CF3- or C2F5-group in the alpha position were transformed into the corresponding chiral thioamides by the reaction with hydrogen sulfide. Subsequent reaction with alpha bromo- or chloro-substituted carbonyls allowed obtaining perfluoroalkylated analogues of natural thiazole-containing cyclic amines in high isolated yield and up to > 99 % ee.