丁烯内酯
对映选择合成
化学
钯
天然产物
催化作用
立体异构
选择性
组合化学
功能群
内酯
立体化学
有机化学
聚合物
作者
Sanliang Li,Qiaoyu Chen,Junfeng Yang,Junliang Zhang
标识
DOI:10.1002/anie.202202046
摘要
γ-Butenolide and γ-butyrolactone scaffolds are two types of important core structures in numerous natural products and bioactive targets. However, methods to construct the chiral quaternary arylated γ-butenolide are rarely explored. We herein report an efficient Pd-catalyzed enantioselective γ-arylation of β,γ-unsaturated butenolides with aryl bromides, which shows high γ-selectivity, good functional group tolerance and excellent enantioselectivity. Notably, this protocol also allows for facile construction of tricyclic tetrahydroindolines and tetrahydroisoquinolinones in one step. DFT calculations are consistent with the experimental results, suggesting that the γ-arylation is favoured over the α-arylation. Finally, this method is applied to the rapid synthesis of natural product (R)-(+)-boivinianin A.
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