• DOI:10.1021/OL030045F
• Corpus ID: 171408

Oxidative 5-endo cyclization of enamides mediated by ceric ammonium nitrate.

@article{Clark2003Oxidative5C,
  title={Oxidative 5-endo cyclization of enamides mediated by ceric ammonium nitrate.},
  author={Andrew J. Clark and Colin P. Dell and John M. McDonagh and Joanna V. Geden and Peter Mawdsley},
  journal={Organic letters},
  year={2003},
  volume={5 12},
  pages={
          2063-6
        }
}

• A. Clark, C. Dell, +2 authors Peter Mawdsley
• Published 9 May 2003
• Chemistry
• Organic letters

[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.