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一种温和的催化合成2-恶唑啉的方法:氧杂环丁烷开环反应,可快速获得多种天然产物。

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

作者信息

Huang Hai, Yang Wen, Chen Zuliang, Lai Zengwei, Sun Jianwei

机构信息

Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology , School of Petrochemical Engineering , Changzhou University , Changzhou 213164 , China . Email:

Department of Chemistry and Shenzhen Research Institute , The Hong Kong University of Science and Technology , Clear Water Bay , Kowloon , Hong Kong SAR , China.

出版信息

Chem Sci. 2019 Aug 26;10(41):9586-9590. doi: 10.1039/c9sc03843d. eCollection 2019 Nov 7.

Abstract

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), 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.

摘要

公开了一种从氧杂环丁烷快速合成恶唑啉的新催化方法。这种温和的方法补充了基于β-羟基或不饱和酰胺的非催化环化的传统恶唑啉合成方法。它也是氧杂环丁烷反应活性谱中导致杂环形成的新成员。在三氟甲磺酸铟的存在下,各种3-氨基氧杂环丁烷顺利进行分子内环化反应,形成相应的2-恶唑啉,包括一些有价值的基于恶唑啉的双齿配体。该方法还提供了快速获得各种天然产物和抗菌分子的途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b511/6993743/be3679ac9935/c9sc03843d-f1.jpg

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