Copper-mediated anomeric O-arylation with organoboron reagents. Issue 23 (24th May 2019)

• Record Type: Journal Article
• Authors: Dimakos, Victoria; Liu, Jacklyn J. W.; Ge, Zhenlu; Taylor, Mark S.
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 23(2019)
• Page Start: 5671
• Page End: 5674
• Publication Date: 2019-05-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01022j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Copper-mediated couplings of boroxines with glycosyl hemiacetals generate O -aryl glycosides via Csp 2 –O bond formation. Abstract : Copper-mediated couplings of arylboroxines with glycosyl hemiacetals furnish O -aryl glycosides via Csp 2 –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.