环丙烷化
环丙烷
分子内力
碳化物
化学
重氮
立体化学
组合化学
戒指(化学)
催化作用
药物化学
有机化学
铑
作者
Yulong Wang,Shenyu Shen,Chonglong He,Youkang Zhou,Keyuan Zhang,Bin Rao,Tian Han,Xin‐Hua Duan,Yaqiong Su,Le Liu
出处
期刊:Chemical Science
[The Royal Society of Chemistry]
日期:2023-01-01
卷期号:14 (24): 6663-6668
被引量:1
摘要
Cyclopropane-fused ring scaffolds represent one of the most appealing structural motifs in organic chemistry due to their wide presence in bioactive molecules and versatility in organic synthesis. These skeletons are typically prepared from olefinic diazo compounds via transition-metal catalysed intramolecular carbenoid insertion, which suffers from prefunctionalization of starting materials and limited substrate scope. Herein, we disclose a practical copper-mediated direct intramolecular cyclopropanation of distal olefinic acetate to synthesize cyclopropane-fused γ-lactones and lactams. This cascade reaction is postulated to proceed through a hydrogen atom transfer event induced radical cyclization and copper-mediated cyclopropanation sequence. The protocol features high atom- and step-economy, excellent diastereoselectivity, broad tolerance of functional groups, and operational simplicity.
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