Organic Chemistry Portal



Lewis Acid Catalyzed Indole Synthesis via Intramolecular Nucleophilic Attack of Phenyldiazoacetates to Iminium Ions

Lei Zhou and Michael P. Doyle*

*Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, Email:

L. Zhou, M. P. Doyle, J. Org. Chem., 2009, 74, 9222-9224.

DOI: 10.1021/jo902089e (free Supporting Information)


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.

see article for more examples

Key Words

Diazo Esters, Indoles

ID: J42-Y2009-3550