1.
J Org Chem
; 89(2): 1310-1314, 2024 Jan 19.
Artigo
em Inglês
| MEDLINE
| ID: mdl-38170997
RESUMO
We report an efficient route for the synthesis of highly substituted 1-aminonaphthalenes from benzaldehydes. The method employs a stereoselective Still-Gennari modification of the Horner-Wadsworth-Emmons olefination to afford (E)-benzylidenesuccinonitrile precursors, which undergo Bronsted acid mediated benzannulation to afford 1-aminonaphthalene derivatives in 35-95% yield. The abundance of commercially available benzaldehydes, coupled with the simplicity of our method, enables many previously unexplored naphthalene substitution patterns to become readily accessible.