Visible‐Light‐Promoted Decarboxylative Giese Reactions of α‐Aryl Ethenylphosphonates and the Application in the Synthesis of Fosmidomycin Analogue,Advanced Synthesis & Catalysis

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Visible‐Light‐Promoted Decarboxylative Giese Reactions of α‐Aryl Ethenylphosphonates and the Application in the Synthesis of Fosmidomycin Analogue
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-02-07 , DOI: 10.1002/adsc.201701285
Ting Guo ₁ , Li Zhang ₂ , Yewen Fang _{3,

4} , Xiaoping Jin ₅ , Yan Li ₁ , Ruifeng Li ₂ , Xie Li ₃ , Wu Cen ₃ , Xiaobo Liu ₃ , Zongming Tian ₅

Affiliation

An approach for the synthesis of α‐aryl alkylphosphonates based on visible‐light photocatalytic Giese reaction of α‐aryl vinylphosphonates with aliphatic carboxylic acids has been successfully developed. This protocol tolerates a wide range of functional groups and shows broad substrate scope with regard to both the carboxylic acid and vinylphosphonate components. With sequential Giese/hydrolysis reactions as the strategy, the oxo‐phosphonates could be easily accessible. The synthetic application of the hydroformylation reaction was demonstrated by the synthesis of the intermediate of α‐phenyl substituted fosmidomycin analogue. Furthermore, the competitive decarboxylative alkylation of vinylphosphonate and acrylate was also investigated.

中文翻译：

α-芳基乙烯基膦酸酯的可见光促进的脱羧吉斯反应及其在合成磷霉素类似物中的应用

已经成功开发了一种基于α-芳基乙烯基膦酸酯与脂肪族羧酸的可见光光催化吉斯反应的合成α-芳基烷基膦酸酯的方法。该方案可耐受各种官能团，并且在羧酸和乙烯基膦酸酯组分方面均显示出广泛的底物范围。通过顺序进行Giese /水解反应作为策略，氧代膦酸酯很容易获得。加氢甲酰化反应的合成应用通过α-苯基取代的磷霉素类似物中间体的合成得到证明。此外，还研究了乙烯基膦酸酯和丙烯酸酯的竞争性脱羧烷基化。

更新日期：2018-02-07

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