Stereoselective Synthesis of New Vicinal Diaminoalkyl Naphthols by Three Component Mannich Type Reaction of α,β-Unsaturated Aldehydes.

Abstract The application of the aromatic Mannich reaction to α,β-unsaturated aldehydes, affords a series of new diaminoalkyl naphthols, by a convenient solventless reaction, starting from inexpensive and easily available starting materials. The absolute configurations of the products obtained are attributed on the basis of the coupling constant values of 1 H NMR spectra, joined with the conformational analysis of the molecules by molecular modelling. A mechanistic hypothesis is proposed, which involves an imino–amino intermediate.