Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones

[Image: see text] A silver-assisted method for [3 + 2] annulation of nitrones with isocyanides has been developed. The developed protocol allows access to a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-one derivatives as single diastereomers in good to excellent yields using silver oxide as...

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Autores principales: Shen, Xuanyu, Shatskiy, Andrey, Chen, Yan, Kärkäs, Markus D., Wang, Xiang-Shan, Liu, Jian-Quan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7307928/
https://www.ncbi.nlm.nih.gov/pubmed/32013428
http://dx.doi.org/10.1021/acs.joc.9b03279
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author Shen, Xuanyu
Shatskiy, Andrey
Chen, Yan
Kärkäs, Markus D.
Wang, Xiang-Shan
Liu, Jian-Quan
author_facet Shen, Xuanyu
Shatskiy, Andrey
Chen, Yan
Kärkäs, Markus D.
Wang, Xiang-Shan
Liu, Jian-Quan
author_sort Shen, Xuanyu
collection PubMed
description [Image: see text] A silver-assisted method for [3 + 2] annulation of nitrones with isocyanides has been developed. The developed protocol allows access to a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-one derivatives as single diastereomers in good to excellent yields using silver oxide as the catalyst and molecular oxygen as the terminal oxidant. A plausible mechanism involving a nucleophilic addition/cyclization/protodeargentation/oxidation pathway is proposed on the basis of experimental results.
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spelling pubmed-73079282020-06-23 Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones Shen, Xuanyu Shatskiy, Andrey Chen, Yan Kärkäs, Markus D. Wang, Xiang-Shan Liu, Jian-Quan J Org Chem [Image: see text] A silver-assisted method for [3 + 2] annulation of nitrones with isocyanides has been developed. The developed protocol allows access to a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-one derivatives as single diastereomers in good to excellent yields using silver oxide as the catalyst and molecular oxygen as the terminal oxidant. A plausible mechanism involving a nucleophilic addition/cyclization/protodeargentation/oxidation pathway is proposed on the basis of experimental results. American Chemical Society 2020-02-04 2020-03-06 /pmc/articles/PMC7307928/ /pubmed/32013428 http://dx.doi.org/10.1021/acs.joc.9b03279 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Shen, Xuanyu
Shatskiy, Andrey
Chen, Yan
Kärkäs, Markus D.
Wang, Xiang-Shan
Liu, Jian-Quan
Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones
title Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones
title_full Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones
title_fullStr Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones
title_full_unstemmed Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones
title_short Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones
title_sort silver-assisted [3 + 2] annulation of nitrones with isocyanides: synthesis of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-ones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7307928/
https://www.ncbi.nlm.nih.gov/pubmed/32013428
http://dx.doi.org/10.1021/acs.joc.9b03279
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