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

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. (C) 2003 Elsevier Science Ltd. All rights reserved.