Selective Functionalization of Norbornadiene Through Nitrile Oxide Cycloaddition/Ring‐Opening/Cross‐Metathesis Protocols

This work describes a study on the selective functionalization of norbornadiene across nitrile oxide 1,3‐dipolar cycloaddition/ring‐opening (ROM)/cross‐metathesis (CM) protocols. Readily available norbornadiene was transformed into novel bicyclic scaffolds with multiple chiral centers. The described...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2021-05, Vol.10 (5), p.1184-1191
Main Authors: Benke, Zsanett, Remete, Attila M., Semghouli, Anas, Kiss, Loránd
Format: Article
Language:English
Subjects:
Cycloaddition
functionalization
isoxazoline
Metathesis
Organic chemistry
selectivity
Substrates
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Summary:This work describes a study on the selective functionalization of norbornadiene across nitrile oxide 1,3‐dipolar cycloaddition/ring‐opening (ROM)/cross‐metathesis (CM) protocols. Readily available norbornadiene was transformed into novel bicyclic scaffolds with multiple chiral centers. The described syntheses involved selective cycloadditions followed by ring‐opening metathesis of the resulting cycloalkane‐fused isoxazoline derivatives, and selective cross‐metathesis by chemodiscrimination of the C=C bonds of the resulting alkenylated heterocycles. The cross‐metathesis transformations have been studied under various experimental conditions with the aim of exploring the substrate influence and chemodifferentiation of the olefin bonds providing the corresponding functionalized isoxazoline derivatives. Chemodiscrimination of C=C bonds of various diolefinated cyclopentane‐fused isoxazolines has been investigated across cross‐metathesis. The transformations have been found to be substrate and catalyst dependent.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202100147