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钴(II)催化的 C(sp )-C(sp ) 偶联反应用于直接立体选择性合成 2-脱氧-C-糖苷

Cobalt(II)-Catalyzed C(sp )-C(sp ) Coupling for the Direct Stereoselective Synthesis of 2-Deoxy-C-Glycosides from Glycals.

机构信息

China Pharmaceutical University, 639 Longmian Avenue, Jiangning District, Nanjing, 211198, China.

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai, 201203, China.

出版信息

Angew Chem Int Ed Engl. 2023 May 22;62(22):e202300424. doi: 10.1002/anie.202300424. Epub 2023 Apr 13.

Abstract

We report a ligand-controlled Co -catalyzed C(sp )-C(sp ) coupling hydroalkylation for direct and β-selective synthesis of 2-deoxy-C-glycosides from glycals. This reaction proceeds by a radical pathway for alkyl halide activation and is β-selective through ligand control. This approach may inspire the development of further stereoselective coupling reactions with potential application in the field of carbohydrates.

摘要

我们报告了一种配体控制的钴催化 C(sp )-C(sp )偶联氢烷基化反应,用于直接和β选择性地从糖醛制备 2-脱氧-C-糖苷。该反应通过自由基途径进行卤代烷烃的活化,并且通过配体控制实现β选择性。这种方法可能会激发进一步的立体选择性偶联反应的发展,具有在碳水化合物领域的潜在应用。

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