Stereoselective Preparation of α‑C‑Vinyl/Aryl Glycosides via Nickel-Catalyzed Reductive
Coupling of Glycosyl Halides with Vinyl and Aryl Halides
Posted on 2018-12-10 - 11:48
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.
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Liu, Jiandong; Gong, Hegui (2018). Stereoselective Preparation of α‑C‑Vinyl/Aryl Glycosides via Nickel-Catalyzed Reductive
Coupling of Glycosyl Halides with Vinyl and Aryl Halides. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b03567
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