Synthesis of 3-Aryl-1-trifluoromethyltetrahydroisoquinolines by Bronsted Acid-Catalyzed C(sp(3))-H Bond Functionalization

摘要

A concise route to 3-aryl-1-trifluoromethyltetrahydroisoquinolines by a benzylic [1,5]-hydride shift-mediated C-H bond functionalization was developed. The [1,5]-hydride shift of the benzylic C(sp(3))-H bond to the trifluoromethylketimine derived from para-anisidine occurred smoothly to produce cis-1-trifluoromethyl-3-aryltetrahydroisoquinolines in good to excellent chemical yields with good diastereoselectivities. In contrast, use of the N-H ketimine furnished N-unprotected tetrahydroisoquinolines in good yields in favor of the trans-isomer.