Catalytic Enantioselective Desymmetrization of Prochiral Triacylamines via Pseudopeptidic Guanidine-Guanidinium Catalysis.
Hu QuXin-Shen LiangWen-Juan WangXian-He ZhaoYu-Hua DengXian-Tao AnWen-Dao ChuXiang-Zhi ZhangChun-An FanPublished in: Organic letters (2022)
Triacylamines with C s symmetry have been explored in asymmetric organocatalysis, leading to the development of a novel catalytic enantioselective desymmetrization of prochiral triacylamines by methanolysis under the catalysis of chiral pseudopeptidic guanidine-guanidinium salt having a weakly coordinating anion. This organocatalytic methodology provides an effective approach to the synthetically useful chiral imide-esters with a 1,5-dicarbonyl moiety, and its synthetic potential has been manifested in the asymmetric synthesis of two GABA analogue drugs, ( R )-Baclofen·HCl and ( S )-Pregabalin.