硝酸铈铵介导的烯酰胺的氧化5-内型环化反应。

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

作者信息

Clark Andrew J, Dell Colin P, McDonagh John M, Geden Joanna, Mawdsley Peter

机构信息

Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK.

出版信息

Org Lett. 2003 Jun 12;5(12):2063-6. doi: 10.1021/ol030045f.

DOI:10.1021/ol030045f

PMID:12790529

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.

摘要

[反应：见正文]硝酸铈铵介导β-烯酰胺酯的氧化5-内型自由基-极性交叉反应，生成5,5-C,O-二取代-γ-内酰胺。根据反应条件，捕获中间体阳离子可得到5-羟基-或5-烷氧基-γ-内酰胺。该方法用于合成天然产物L-755,807、喹乳酸C和PI-091的基本杂环片段。