Stereoselective 1,2-cis Furanosylations Catalyzed by Phenanthroline.

ABSTRACT: Stereoselective formation of the 1,2-cis furanosidic linkage, a motif of many biologically relevant oligosaccharides and polysaccharides, remains an important synthetic challenge. We herein report a new stereoselective 1,2-cis furanosylation method promoted by phenanthroline catalysts under mild and operationally simple conditions. NMR experiments and density functional theory calculations support an associative mechanism in which the rate-determining step occurs from an inverted displacement of the faster-reacting phenanthrolinium ion intermediate with an alcohol nucleophile. The phenanthroline catalysis system is applicable to a number of furanosyl bromide donors to provide the challenging 1,2-cis substitution products in good yield with high anomeric selectivities.

SUBMITTER: Xu H 

PROVIDER: S-EPMC9093562 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature