A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines

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 multip...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2021-08, Vol.17 (1), p.2051-2066
Main Authors: Benke, Zsanett, Remete, Attila M, Kiss, Loránd
Format: Article
Language:English
Subjects:
Catalysts
Chemistry
Cyclopentane
Fluorine
Full Research Paper
functionalization
Investigations
metathesis
nitrile oxide
organofluorine chemistry
selectivity
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Summary: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.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.17.132