Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines.
The four-component Hantzsch reaction provides access to pharmaceutically important dihydropyridines. To expand the utility of this method, we have developed a route under organocatalytic conditions with good yields and excellent ee's. Through catalyst screening, we found that a BINOL-phosphoric acid allowed enantioselective synthesis of six-membered heterocycles with a variety of substitution patterns.
Evans
Christopher G
CG
Department of Pathology and the Life Sciences Institute, University of Michigan, 210 Washtenaw Avenue, Ann Arbor, Michigan 48109, USA.
Gestwicki
Jason E
JE
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004095:Dihydropyridines; D010756:Phosphoric Acids; D011108:Polymers; D011804:Quinolines