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An iron-catalysed radical cyclization/C(sp3)–H alkylation cascade between γ,δ-unsaturated oxime esters and glycine derivatives: access to pyrroline-containing amino acids
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2022-11-25 , DOI: 10.1039/d2qo01543a
Fangyuan Yu 1 , Sen Yang 1 , Zihao Xie 1 , Dengfu Lu 1 , Yuefa Gong 1
Affiliation  

An iron-catalysed selective C(sp3)–H alkylation method for glycine derivatives is reported. Using γ,δ-unsaturated oxime esters as both the alkylation reagent and terminal oxidant, N-aryl glycinates could be converted into a series of pyrroline-containing amino esters with a readily available iron catalyst and a phenanthroline-based ligand. Control experiments showed that the ligand plays a key role in tuning the chemoselectivity, while a radical–polar crossover pathway is proposed according to the mechanistic studies. Additionally, the products obtained with this method could be transformed into various valuable building blocks, including amino acids, amino alcohols and γ-lactams.

中文翻译:

γ,δ-不饱和肟酯和甘氨酸衍生物之间的铁催化自由基环化/C(sp3)–H 烷基化级联反应:获得含吡咯啉的氨基酸

报道了一种用于甘氨酸衍生物的铁催化选择性 C (sp 3 ) –H 烷基化方法。使用 γ,δ-不饱和肟酯作为烷基化试剂和末端氧化剂,N-芳基甘氨酸盐可以在易于获得的铁催化剂和菲咯啉基配体的作用下转化为一系列含吡咯啉的氨基酯。对照实验表明配体在调节化学选择性中起着关键作用,而根据机理研究提出了自由基-极性交叉途径。此外,用这种方法获得的产品可以转化为各种有价值的结构单元,包括氨基酸、氨基醇和 γ-内酰胺。
更新日期:2022-11-25
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