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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Online Access: | https://doi.org/10.3762/bjoc.17.132 |
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doaj-070dca907c6445aeb47bca707e5486e02021-09-13T09:24:29ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-08-011712051206610.3762/bjoc.17.1321860-5397-17-132A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolinesZsanett Benke0Attila M. Remete1Loránd Kiss2Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, HungaryThis 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.https://doi.org/10.3762/bjoc.17.132functionalizationmetathesisnitrile oxideorganofluorine chemistryselectivity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Zsanett Benke Attila M. Remete Loránd Kiss |
spellingShingle |
Zsanett Benke Attila M. Remete Loránd Kiss A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines Beilstein Journal of Organic Chemistry functionalization metathesis nitrile oxide organofluorine chemistry selectivity |
author_facet |
Zsanett Benke Attila M. Remete Loránd Kiss |
author_sort |
Zsanett Benke |
title |
A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines |
title_short |
A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines |
title_full |
A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines |
title_fullStr |
A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines |
title_full_unstemmed |
A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines |
title_sort |
study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2021-08-01 |
description |
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. |
topic |
functionalization metathesis nitrile oxide organofluorine chemistry selectivity |
url |
https://doi.org/10.3762/bjoc.17.132 |
work_keys_str_mv |
AT zsanettbenke astudyonselectivetransformationofnorbornadieneintofluorinatedcyclopentanefusedisoxazolines AT attilamremete astudyonselectivetransformationofnorbornadieneintofluorinatedcyclopentanefusedisoxazolines AT lorandkiss astudyonselectivetransformationofnorbornadieneintofluorinatedcyclopentanefusedisoxazolines AT zsanettbenke studyonselectivetransformationofnorbornadieneintofluorinatedcyclopentanefusedisoxazolines AT attilamremete studyonselectivetransformationofnorbornadieneintofluorinatedcyclopentanefusedisoxazolines AT lorandkiss studyonselectivetransformationofnorbornadieneintofluorinatedcyclopentanefusedisoxazolines |
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1717381075717586944 |