A Synthetic Route to Highly Substituted 1-Aminonaphthalenes from Readily Available Benzaldehydes.

ABSTRACT

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.