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Iron(ΙΙΙ) Catalyzed Aerobic Cα–Cβ Cleavage of Allylic Alcohols
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-18 , DOI: 10.1002/ejoc.202400556
Christos I. Stathakis 1 , Georgia G. Bagkavou 2
Affiliation  

The regiospecific Cα–Cβ cleavage of allylic alcohols under modified aerobic Mukaiyama hydration conditions is presented. The new methodology can be regarded as an equivalent of a two-step process, a typical hydration of the parent allylic alcohol followed by a 1,2-diol cleavage. A broad scope of substrates, both cyclic and acyclic, are applicable, thus introducing substantial structural modification to the core, especially of the former type of substrates. Mechanistic investigation of the reaction reveals the importance of the nearby hydroxyl group for the deviation from the typical Mukaiyama hydration pathway.

中文翻译:


铁(IIII)催化烯丙醇的有氧Cα-Cβ裂解



提出了在改良的有氧 Mukaiyama 水合条件下烯丙醇的区域特异性 Cα-Cβ 裂解。新方法可以被视为相当于两步过程,即母体烯丙醇的典型水合,然后是 1,2-二醇裂解。适用范围广泛的底物,包括环状和非环状的,从而对核心引入实质性的结构修饰,尤其是前一种类型的底物。反应机理研究揭示了附近羟基对于偏离典型 Mukaiyama 水合途径的重要性。
更新日期:2024-06-18
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