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Article

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

by
Xin Zhou
,
Baiyi Mao
and
Zhanbin Zhang
*
College of Chemistry, Beijing Normal University, Beijing 100875, China
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(4), 857; https://doi.org/10.3390/molecules26040857
Submission received: 17 January 2021 / Revised: 2 February 2021 / Accepted: 3 February 2021 / Published: 6 February 2021
(This article belongs to the Section Organic Chemistry)
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Abstract

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.
Keywords: azetidine; oxazoline; isomerization; amide; acid azetidine; oxazoline; isomerization; amide; acid

Share and Cite

MDPI and ACS Style

Zhou, X.; Mao, B.; Zhang, Z. Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines. Molecules 2021, 26, 857. https://doi.org/10.3390/molecules26040857

AMA Style

Zhou X, Mao B, Zhang Z. Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines. Molecules. 2021; 26(4):857. https://doi.org/10.3390/molecules26040857

Chicago/Turabian Style

Zhou, Xin, Baiyi Mao, and Zhanbin Zhang. 2021. "Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines" Molecules 26, no. 4: 857. https://doi.org/10.3390/molecules26040857

APA Style

Zhou, X., Mao, B., & Zhang, Z. (2021). Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines. Molecules, 26(4), 857. https://doi.org/10.3390/molecules26040857

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