Chiral Bicyclic Imidazole Nucleophilic Catalysts: Design, Synthesis, and Application to the Kinetic Resolution of Arylalkylcarbinols

Abstract A new type of chiral 5‐aminoimidazole nucleophilic catalyst, designated as Alkyl‐PDPI (PDPI=3‐pyrrolidinyl‐6,7‐dihydro‐5 H ‐pyrrolo[1,2‐ a ]imidazole), was rationally designed, synthesized and applied to the kinetic resolution of various arylalkylcarbinols with good to excellent enantioselectivities. In particular, for phenyl( tert ‐butyl)methanol and 1‐mesitylethanol, the s factors are as high as 45 and 67, respectively. Additionally, this new kind of chiral imidazole catalyst also showed good enantioselectivity for heteroarylalkylcarbinols. magnified image