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Oxidative 5-endo cyclization of enamides mediated by ceric ammonium nitrate
Andrew J Clark1, Colin P Dell, John M McDonagh
1Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK. msrir@csv.warwick.ac.uk
Organic Letters
|June 7, 2003
Abstract:
[reaction: see text] Ceric ammonium nitrate mediates the oxidative 5-endo radical-polar crossover reactions of beta-enamide esters to give 5,5-C,O-disubstituted-gamma-lactams. Trapping of the intermediate cations leads to 5-hydroxy- or 5-alkoxy-gamma-lactams depending upon the reaction conditions. The methodology was used to synthesize the basic heterocyclic ring fragments of the natural products L-755,807, Quinolacticin C, and PI-091.