Lewis acid catalyzed indole synthesis via intramolecular nucleophilic attack of phenyldiazoacetates to iminium ions.
Lewis acids catalyze the cyclization of methyl phenyldiazoacetates with an ortho-imino group, prepared from o-aminophenylacetic acid, to give 2,3-substituted indoles in quantitative yields.
Zhou
Lei
L
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Doyle
Michael P
MP
D000143:Acids; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007097:Imines; D007211:Indoles / Q000138:chemical synthesis*; D010648:Phenylacetates / Q000737:chemistry*
D000143:Acids; D001391:Azo Compounds; D007097:Imines; D007211:Indoles; D010648:Phenylacetates; C414091:methyl phenyldiazoacetate