镍电催化糖基供体活化使α- c -烯基糖苷组装成为可能。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-09 DOI:10.1021/acs.orglett.5c03327

Fabian Hinrichs,Rajeshwaran Purushothaman,Lutz Ackermann

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引用次数: 0

摘要

c -烯基糖苷是一类重要的碳水化合物，包括许多具有生物活性的化合物。我们开发了一种立体选择性和可持续的策略，使用异头糖基卤化物作为还原烯基化的自由基前体。这使得通过配体控制具有优异α-选择性的有效的端粒功能化成为可能。电化学卤素原子转移（e-XAT）激活糖基供体，避免了化学计量金属还原剂和昂贵的光催化剂。该方法显示出广泛的底物范围，包括多种低聚糖，具有高收率和立体选择性。

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Nickelaelectro-Catalyzed Glycosyl-Donor Activation Enabling α-C-Alkenyl Glycoside Assembly.

C-alkenyl glycosides represent an important class of carbohydrates that includes numerous biologically active compounds. We developed a stereoselective and sustainable strategy using anomeric glycosyl halides as radical precursors for reductive alkenylation. This enables efficient anomeric functionalization with excellent α-selectivity through ligand control. Electrochemical halogen-atom transfer (e-XAT) activates the glycosyl donors, avoiding stoichiometric metal reductants and expensive photocatalysts. This method shows broad substrate scope, including diverse oligosaccharides, delivering high yields and stereoselectivity.

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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.