Site-Selective C6-β-Aminoalkylation of Tetrahydroquinolines with N -Arylsulfonyl Aryl Aziridines in Hexafluoroisopropanol: A Modular Approach to C6-Alkylated Quinolines
Abstract
High Resolution Image Download MS PowerPoint Slide We report a metal-free method for the site-selective C6-β-aminoalkylation of tetrahydroquinolines using N -arylsulfonyl aziridines in HFIP at room temperature. HFIP activates aziridines through hydrogen bonding, promoting a regioselective S N 2-type ring opening. The method features broad functional group tolerance, high yields (up to 89%), and full stereochemical fidelity with chiral aziridines. Gram-scale synthesis with solvent recovery highlights its practicality, while postsynthetic oxidation provides direct access to C6-alkylated quinolines.
Fields of Study & Subjects
Synthesis and Catalytic Reactions
Catalytic C–H Functionalization Methods
Asymmetric Hydrogenation and Catalysis
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 3
- Pages
- 1405–1411
- Publication date
- 9 January 2026
- Language
- EN