Iron-Catalyzed Stereospecific Heterocycle N-Glycosylation with Glycal Epoxides

Stereospecific N-glycosylation of heterocycles with glycal epoxides could readily provide valuable building blocks for drug discovery, but heterocycle N-glycosylation with a pyranose-based glycal epoxide is still difficult using existing methods. We report herein an iron-catalyzed stereospecific heterocycle N-glycosylation method for these glycal epoxides in high yields with low catalyst loadings. This method is functional-group-tolerant and effective for a wide variety of functionalized, complex glycal epoxides and heterocycles.