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- Title
Ligand‐Controlled Stereoselective Synthesis of 2‐Deoxy‐β‐C‐glycosides by Cobalt Catalysis.
- Authors
Liu, Bingxue; Liu, Deguang; Rong, Xianle; Lu, Xi; Fu, Yao; Liu, Qiang
- Abstract
2‐Deoxy‐β‐C‐glycosides represent an important class of carbohydrates that are present in many bioactive molecules. However, owing to the lack of substituents at the C2 position, the stereoselective synthesis of 2‐deoxy‐β‐C‐glycosides is highly challenging. Herein, we report a ligand‐controlled stereoselective C‐alkyl glycosylation reaction to access 2‐deoxy‐β‐C‐alkyl glycosides from readily available glycals and alkyl halides. This method exhibits broad substrate scope and excellent diastereoselectivity under very mild conditions. In addition, unprecedented stereodivergent synthesis of 2‐deoxy‐C‐ribofuranosides is achieved using different chiral bisoxazoline ligands. Mechanistic studies suggest that hydrometallation of the glycal with the bisoxazoline‐ligated Co−H species may be the turnover‐limiting and stereodetermining step of this transformation.
- Subjects
COBALT; CATALYSIS; HALOALKANES; COUPLING reactions (Chemistry); GLYCALS; GLYCOSIDES
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 22, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202218544