This work presents an examination of the selective functionalization of norbornadiene through nitrile oxide 1,3-dipolar cycloaddition/ring-opening metathesis (ROM)/cross-metathesis (CM) protocols. Functionalization of commercially available norbornadiene provided novel bicyclic scaffolds with multiple stereogenic centers. The synthesis involved selective cycloadditions, with subsequent ROM of the formed cycloalkene-fused isoxazoline scaffolds and selective CM by chemodifferentiation of the olefin bonds of the resulting alkenylated derivatives. Various experimental conditions were applied for the CM transformations with the goal of exploring substrate and steric effects, catalyst influence and chemodifferentiation of the olefin bonds furnishing the corresponding functionalized, fluorine-containing isoxazoline derivatives.

中文翻译：

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降冰片二烯选择性转化为氟化环戊烷稠合异恶唑啉的研究

这项工作通过氧化腈 1,3-偶极环加成/开环复分解 (ROM)/交叉复分解 (CM) 协议对降冰片二烯的选择性功能化进行了检查。市售降冰片二烯的功能化提供了具有多个立体中心的新型双环支架。合成涉及选择性环加成，随后形成的环烯烃稠合异恶唑啉支架的 ROM 和通过所得烯基化衍生物的烯烃键的化学分化选择性 CM。CM 转化应用了各种实验条件，目的是探索底物和空间效应、催化剂影响和烯烃键的化学分化，提供相应的官能化含氟异恶唑啉衍生物。