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Photocatalytic Enantioselective Radical Cascade Multicomponent Minisci Reaction of β-Carbolines Using Diazo Compounds as Radical Precursors
Advanced Science ( IF 15.1 ) Pub Date : 2024-04-19 , DOI: 10.1002/advs.202402272
Yi‐Jie Gu 1, 2 , Mu‐Peng Luo 1 , Hua Yuan 2 , Guo‐Kai Liu 3 , Shou‐Guo Wang 1
Affiliation  

Here, a photocatalytic asymmetric multicomponent cascade Minisci reaction of β-carbolines with enamides and diazo compounds is reported, enabling an effective enantioselective radical C─H functionalization of β-carbolines with high yields and enantioselectivity (up to 83% yield and 95% ee). This enantioselective multicomponent Minisci protocol exhibits step economy, high chemo-/enantio-selective control, and good functional group tolerance, allowing access to a variety of valuable chiral β-carbolines. Notably, diazo compounds are suitable radical precursors in enantioselective cascade radical reactions. Moreover, the efficiency and practicality of this approach are demonstrated by the asymmetric synthesis of bioactive compounds and natural products.

中文翻译:

使用重氮化合物作为自由基前体的 β-咔啉的光催化对映选择性自由基级联多组分微型反应

在此,报道了 β-咔啉与烯酰胺和重氮化合物的光催化不对称多组分级联 Minisci 反应,实现了 β-咔啉的有效对映选择性自由基 C─H 官能化,具有高产率和对映选择性(高达 83% 产率和 95% ee) 。这种对映选择性多组分 Minisci 方案具有步骤经济性、高化学/对映选择性控制和良好的官能团耐受性,允许获得各种有价值的手性 β-咔啉。值得注意的是,重氮化合物是对映选择性级联自由基反应中合适的自由基前体。此外,生物活性化合物和天然产物的不对称合成证明了该方法的效率和实用性。
更新日期:2024-04-24
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