Stereoselective Synthesis of C-Vinyl Glycosides via Palladium-Catalyzed C-H Glycosylation of Alkenes

C-vinyl glycosides are an important class of carbohydrates and pose a unique synthetic challenge. A new strategy has been developed for stereoselective synthesis of C-vinyl glycosides via Pd-catalyzed directed C-H glycosylation of alkenes with glycosyl chloride donors using an easily removable bidentate auxiliary. Both the gamma C-H bond of allylamines and the delta C-H bond of homoallyl amine substrates can be glycosylated in high efficiency and with excellent regio- and stereoselectivity. The resulting C-vinyl glycosides can be further converted to a variety of C-alkyl glycosides with high stereospecificity. These reactions offer a broadly applicable method to streamline the synthesis of complex C-vinyl glycosides from easily accessible starting materials.

Automated summary

A new strategy has been developed for the stereoselective synthesis of C-vinyl glycosides, using Pd-catalyzed directed C-H glycosylation. This method offers a broadly applicable approach to streamline the synthesis of complex C-vinyl glycosides with high efficiency and excellent regio- and stereoselectivity.