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

被引：65

作者：

Clark, AJ ^{[1
]}

Dell, CP

McDonagh, JM

Geden, J

Mawdsley, P

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

[2] Lilly Res Ctr Ltd, Windlesham GU20 6PH, Surrey, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 12期

关键词：

D O I：

10.1021/ol030045f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2063 / 2066

页数：4

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