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Stereoselective Preparation of α‑C‑Vinyl/Aryl Glycosides via Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Vinyl and Aryl Halides

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journal contribution
posted on 10.12.2018, 11:48 by Jiandong Liu, Hegui Gong
Facile preparation of the α-C-vinyl and -aryl glycosides has been developed via mild Ni-catalyzed reductive vinylation and arylation of C1-glycosyl halides with vinyl/aryl halides. Good to high α-selectivities were achieved for C-glucosides, galactosides, maltoside, and mannosides, which were dictated by the employment of pyridine type ligands. As such, the present work represents unprecedented control for a high level of α-selectivity for C-vinyl-glucosides using cross-coupling approaches and offers hitherto optimal α-selective preparation of C-aryl glucosides via catalyst-controlled coupling strategies.