Lewis-acid-mediated regioselectivity switching by aromatization-driven rearrangement of 5-amino-1,4-epoxy-1,4-dihydronaphthalenes
Abstract
Selective synthesis of 8- or 5-amino-substituted 1-naphthols through rearrangement is demonstrated using Lewis acids. A variety of tetrasubstituted 1-naphthols were selectively prepared from 2,4-disubstituted 5-amino-1,4-epoxy-1,4-dihydronaphthalenes in a Lewis-acid-dependent manner with AlCl3 or ZnCl2 serving as the activators. A unique reaction mechanism was proposed on the basis of NMR experiments.
Fields of Study & Subjects
Axial and Atropisomeric Chirality Synthesis
Synthesis of heterocyclic compounds
Synthesis of Indole Derivatives
Publication details
- Journal / source
- ChemRxiv
- Publication date
- 9 January 2026
- Document type
- Preprint