A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products

A new catalytic protocol for the expedient synthesis of oxazolines from oxetanes is disclosed. This mild process complements the conventional oxazoline synthesis based on non-catalytic cyclization of β-hydroxy or unsaturated amides. It is also a new addition to the reactivity profile of oxetanes lea...

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Autores principales: Huang, Hai, Yang, Wen, Chen, Zuliang, Lai, Zengwei, Sun, Jianwei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6993743/
https://www.ncbi.nlm.nih.gov/pubmed/32055332
http://dx.doi.org/10.1039/c9sc03843d
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author Huang, Hai
Yang, Wen
Chen, Zuliang
Lai, Zengwei
Sun, Jianwei
author_facet Huang, Hai
Yang, Wen
Chen, Zuliang
Lai, Zengwei
Sun, Jianwei
author_sort Huang, Hai
collection PubMed
description A new catalytic protocol for the expedient synthesis of oxazolines from oxetanes is disclosed. This mild process complements the conventional oxazoline synthesis based on non-catalytic cyclization of β-hydroxy or unsaturated amides. It is also a new addition to the reactivity profile of oxetanes leading to heterocycles. In the presence of In(OTf)(3), various 3-amido oxetanes underwent smooth intramolecular cyclization to form the corresponding 2-oxazolines, including some valuable oxazoline-based bidentate ligands. This protocol also provides rapid access to various natural products and antibacterial molecules.
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spelling pubmed-69937432020-02-13 A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products Huang, Hai Yang, Wen Chen, Zuliang Lai, Zengwei Sun, Jianwei Chem Sci Chemistry A new catalytic protocol for the expedient synthesis of oxazolines from oxetanes is disclosed. This mild process complements the conventional oxazoline synthesis based on non-catalytic cyclization of β-hydroxy or unsaturated amides. It is also a new addition to the reactivity profile of oxetanes leading to heterocycles. In the presence of In(OTf)(3), various 3-amido oxetanes underwent smooth intramolecular cyclization to form the corresponding 2-oxazolines, including some valuable oxazoline-based bidentate ligands. This protocol also provides rapid access to various natural products and antibacterial molecules. Royal Society of Chemistry 2019-08-26 /pmc/articles/PMC6993743/ /pubmed/32055332 http://dx.doi.org/10.1039/c9sc03843d Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Huang, Hai
Yang, Wen
Chen, Zuliang
Lai, Zengwei
Sun, Jianwei
A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products
title A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products
title_full A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products
title_fullStr A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products
title_full_unstemmed A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products
title_short A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products
title_sort mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6993743/
https://www.ncbi.nlm.nih.gov/pubmed/32055332
http://dx.doi.org/10.1039/c9sc03843d
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