Synthesis of enantiopure 1,2-dihydroxyhexahydropyrroloisoquinolines as potential tools for asymmetric catalysis

Abstract The stereocontrolled synthesis of enantiopure 1,2-dihydroxyhexahydropyrroloisoquinolines 2 – 4 and a formal synthesis of ent - 2 – 4 starting from d -mannose and l -tartaric acid is reported. The strong tertiary amine bases 2 – 4 containing hydroxyl groups, able to activate electrophiles through hydrogen bonding, are potentially useful as a catalysts in base-catalyzed processes as well as new ligands in metal-based catalysis.