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Oxidative 5-endo cyclization of enamides mediated by ceric ammonium nitrate
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UNSPECIFIED. (2003) Oxidative 5-endo cyclization of enamides mediated by ceric ammonium nitrate. ORGANIC LETTERS, 5 (12). pp. 2063-2066. ISSN 1523-7060
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Official URL: http://dx.doi.org/10.1021/ol030045f
Abstract
Ceric ammonium nitrate mediates the oxidative 5-endo radical-polar crossover reactions of beta-enamide esters to give 5,5-CO-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.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | ORGANIC LETTERS |
| Publisher: | AMER CHEMICAL SOC |
| ISSN: | 1523-7060 |
| Date: | 12 June 2003 |
| Volume: | 5 |
| Number: | 12 |
| Number of Pages: | 4 |
| Page Range: | pp. 2063-2066 |
| Identification Number: | 10.1021/ol030045f |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/9660 |
Data sourced from Thomson Reuters' Web of Knowledge
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