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

Enantioselective synthesis of thiazole‐containing α‐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. Enantioselective synthesis of thiazole‐containing α‐perfluoroalkylated cyclic amines was elaborated. Enantioselective Strecker hydrocyanation followed by the reaction with hydrogen sulfide resulted in highly efficient formation of the corresponding thioamides. Finally, Hantzsch reactions provided access to a family of fluorinated analogues of natural products. [ABSTRACT FROM AUTHOR]