Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation

Abstract

Electron-rich aromatic compounds such as 2-naphthol give a faster and asymmetric 1-aminoalky-lation with high yields when treated with (R)-1-phenylethylamine and aromatic aldehydes in solvent-free conditions. An asymmetric transformation of a second kind, probably induced by the preferential crystallization of one diastereomer, affords the straightforward and stereoselective synthesis of aminoalkylnaphthols. Mechanisms predictable for this asymmetric reaction are reported. The absolute configurations and the conformations of the unknown aminonaphthols are widely ascertained