Copper-mediated anomeric O-arylation with organoboron reagents.
PMID 31123748 · Organic & biomolecular chemistry · 2019 · DOI 10.1039/c9ob01022j
Authors: Victoria Dimakos; Jacklyn J W Liu; Zhenlu Ge; Mark S Taylor
Abstract
Copper-mediated couplings of arylboroxines with glycosyl hemiacetals furnish O-aryl glycosides via Csp2-O bond formation. The method enables the anomeric O-arylation of protected pyranose and furanose derivatives, and is tolerant of functionalized arylboroxine partners. Whereas mixtures of anomers are formed from glucopyranose, galactopyranose and arabinofuranose hemiacetals, the α-anomer is generated selectively from mannopyranose and mannofuranose-derived substrates.
Cite
Victoria Dimakos; Jacklyn J W Liu; Zhenlu Ge; Mark S Taylor. Copper-mediated anomeric O-arylation with organoboron reagents. Organic & biomolecular chemistry (2019). PMID 31123748. DOI 10.1039/c9ob01022j.