糖醛的电化学费里尔重排

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-10-21 DOI:10.1021/acs.orglett.4c03511

Chun Qi, Giulio Goti, Andrea Sartorel, Luca Dell’Amico, Daniele Mazzarella

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引用次数: 0

摘要

费里尔重排（FR）是一种有据可查的反应，它依靠强酸或氧化剂将糖转化为不饱和糖基衍生物。在这项工作中，我们介绍了一种电化学变体的费里尔重排反应，它具有广泛的底物兼容性。各种亲核物和糖醛衍生物都能以高产率和出色的非对映选择性生成 2,3-不饱和糖基衍生物。这种可持续的方法有望拓展电化学在糖化学中的应用。

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Electrochemical Ferrier Rearrangement of Glycals

The Ferrier rearrangement (FR) is a well-documented reaction that relies on strong acids or oxidants to convert glycals into unsaturated glycosyl derivatives. In this work, we introduce an electrochemical variant of the FR, offering a broad substrate compatibility. Various nucleophiles and glycal derivatives afford 2,3-unsaturated glycosyl derivatives in high yields with excellent diastereoselectivities. This sustainable method promises to expand the electrochemistry applications in sugar chemistry.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.