Site-Selective C6-β-Aminoalkylation of Tetrahydroquinolines with <i>N</i>-Arylsulfonyl Aryl Aziridines in Hexafluoroisopropanol: A Modular Approach to C6-Alkylated Quinolines.

ABSTRACT: 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_N2-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.

SUBMITTER: Taskesenligil Y 

PROVIDER: S-EPMC12836323 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature