简便制备含氟 2,3-环氧丙酸酯及其与各种亲核物的环氧开环反应。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-09-25 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.206

Yutaro Miyashita, Sae Someya, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Takashi Yamazaki

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引用次数: 0

摘要

我们在此介绍一种简便的方法，即利用低咀嚼度且易于处理的试剂 NaOCl-5H2O，从相应的烯酸酯开始，获得 3 位含取代基氟的 2,3-环氧酯。由于有关此类 2,3-环氧酯反应性的信息很少，因此我们采用了多种亲核剂打开环氧环，并成功地阐明了这些通过 SN2 机制进行的化学和区域选择性过程，通常以高度反选择性的方式主要生成 2-取代的 3-羟基酯。

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Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles.

We describe herein a facile method to access 2,3-epoxyesters with fluorine-containing substituents at their 3-position starting from the corresponding enoates by utilization of the low-costed and easy-to-handle reagent, NaOCl·5H₂O. Because very little has been disclosed about the reactivity of such 2,3-epoxyesters, their epoxy ring opening by a variety of nucleophiles was carried out and we succeeded in clarifying these chemo- as well as regioselective processes proceeding via the S_N2 mechanism to mainly afford 2-substituted 3-hydroxyesters usually in a highly anti selective manner.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.