Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines

Chiral 2-oxazolines are valuable building blocks and famous ligands for asymmetric catalysis. The most common synthesis involves the reaction of an amino alcohol with a carboxylic acid. In this paper, an efficient synthesis of 2-oxazolines has been achieved via the stereospecific isomerization of 3-...

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Detalles Bibliográficos
Autores principales: Zhou, Xin, Mao, Baiyi, Zhang, Zhanbin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7914936/
https://www.ncbi.nlm.nih.gov/pubmed/33562033
http://dx.doi.org/10.3390/molecules26040857
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author Zhou, Xin
Mao, Baiyi
Zhang, Zhanbin
author_facet Zhou, Xin
Mao, Baiyi
Zhang, Zhanbin
author_sort Zhou, Xin
collection PubMed
description Chiral 2-oxazolines are valuable building blocks and famous ligands for asymmetric catalysis. The most common synthesis involves the reaction of an amino alcohol with a carboxylic acid. In this paper, an efficient synthesis of 2-oxazolines has been achieved via the stereospecific isomerization of 3-amido-2-phenyl azetidines. The reactions were studied in the presence of both Brønsted and Lewis acids, and Cu(OTf)(2) was found to be the most effective.
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spelling pubmed-79149362021-03-01 Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines Zhou, Xin Mao, Baiyi Zhang, Zhanbin Molecules Article Chiral 2-oxazolines are valuable building blocks and famous ligands for asymmetric catalysis. The most common synthesis involves the reaction of an amino alcohol with a carboxylic acid. In this paper, an efficient synthesis of 2-oxazolines has been achieved via the stereospecific isomerization of 3-amido-2-phenyl azetidines. The reactions were studied in the presence of both Brønsted and Lewis acids, and Cu(OTf)(2) was found to be the most effective. MDPI 2021-02-06 /pmc/articles/PMC7914936/ /pubmed/33562033 http://dx.doi.org/10.3390/molecules26040857 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zhou, Xin
Mao, Baiyi
Zhang, Zhanbin
Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines
title Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines
title_full Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines
title_fullStr Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines
title_full_unstemmed Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines
title_short Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines
title_sort synthesis of 2-oxazolines from ring opening isomerization of 3-amido-2-phenyl azetidines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7914936/
https://www.ncbi.nlm.nih.gov/pubmed/33562033
http://dx.doi.org/10.3390/molecules26040857
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AT maobaiyi synthesisof2oxazolinesfromringopeningisomerizationof3amido2phenylazetidines
AT zhangzhanbin synthesisof2oxazolinesfromringopeningisomerizationof3amido2phenylazetidines

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