Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines.
Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel-Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziridinium ions as the key intermediates in the Lewis acid catalyzed FC reactions.
Department of Biological and Chemical Sciences, Illinois Institute of Technology , Chicago, Illinois 60616, United States.
Hyun-Soon
HS
Chong
Yunwei
Y
Chen
D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
D001388:Aziridines; D058116:Lewis Acids; D044005:Tetrahydroisoquinolines