ol8b03567_si_001.pdf (6.29 MB)
Stereoselective Preparation of α‑C‑Vinyl/Aryl Glycosides via Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Vinyl and Aryl Halides
journal contribution
posted on 2018-12-10, 11:48 authored by Jiandong Liu, Hegui GongFacile 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.