Functionalized polar 1,2,4-trioxanes as building blocks by singlet oxygenation of 4-hydroxy tiglic acid using the solvent deuterium isotope trick
Functionalized polar 1,2,4-trioxanes as building blocks by singlet oxygenation of 4-hydroxy tiglic acid using the solvent deuterium isotope trick
复制标题
DOI：
10.1039/c3ra40555a
复制
发表时间：
2013-01-01
期刊：
影响因子：
3.9
通讯作者：
Neudoerfl, Joerg M.
中科院分区：
文献类型：
--
作者：
Griesbeck, Axel G.;Schlundt, Viktor;Neudoerfl, Joerg M.
具有低单线态氧反应性的底物4-羟基惕各酸（1）通过在氘代溶剂中的光氧化转化为1，2-氢过氧醇2，并用于随后的BF 3催化的与无环酮和环状酮的过氧缩醛化。该路线使得能够合成水溶性三恶烷，其是用于进一步官能化的通用结构单元，例如。G.酯和酰胺形成。
The substrate 4-hydroxy tiglic acid (1), which has low singlet oxygen reactivity, is converted to the 1,2-hydroperoxyalcohol 2 by photooxygenation in deuterated solvents and used for subsequent BF3-catalyzed peroxyacetalizations with acyclic and cyclic ketones. This route enables the synthesis of water-soluble trioxanes that are versatile building blocks for further functionalization, e. g. ester and amide formation.