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

Abstract

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.