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

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.

SUBMITTER: Zhou X

PROVIDER: S-EPMC7914936 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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

Zhou Xin X Mao Baiyi B Zhang Zhanbin Z

Molecules (Basel, Switzerland) 20210206 4

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)<sub>2</sub> was found to be the most effective. ...[more]

PMID: 33562033

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