Stereoselective synthesis of vicinal aminodiols,diamines and diaminols by the use of enantiopure aldehydes in the three-component aromatic Mannich-type reaction

A short and stereoselective synthesis of vicinal aminodiols, diamines and diaminols obtained in good yields, through a three-component aromatic Mannich-type reaction, is reported. Enantiopure aldehydes containing stereogenic centres and functionalized with variously protected amino and hydroxy groups successfully afforded enantiopure aminoalkylnaphthols. Conformational analysis, compared with ¹H NMR data of the products obtained, allows the attribution of the absolute configuration, also confirmed by X-ray analysis.