Stereoselective formation of 1,2-cis furanosidic linkage, a motif of many biologically relevant oligosaccharides and polysaccharides, remains an important synthetic challenge. We herein report a new 1,2-cis furanosylation method that is enabled under phenanthroline catalysis and achieved under mild and operationally simple conditions in good yield and with high selectivities. NMR experiments and density-functional theory calculations support an associative mechanism in which rate-determining step occurs from the invertive displacement of the faster reacting phenanthrolinium ion intermediate with alcohol acceptor. The phenanthroline catalysis system is applicable to a number of furanose bromide donors. While arabinofuranose bromide provides beta-1,2-cis products, xylo- and ribofuranose bromides favor alpha-1,2-cis products.

Stereoselective 1,2-cis furanosylations catalyzed by phenanthroline

ACS Spring 2022

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