Stereoselective Synthesis of Indolyl-<i>C</i>-glycosides Enabled by Sequential Aminopalladation and Heck Glycosylation of 2-Alkynylanilines with Glycals
Xiao Xiao, Puren Han, Jie‐Ping Wan, Jianchao Liu
Abstract
-glycosides via aminopalladation and subsequent Heck-type glycosylation of easily available 2-alkynylanilines and glycals has been developed. This protocol features excellent stereoselectivity, a broad substrate scope, and mild reaction conditions. In addition, 2,3-pseudoglycals also successfully participated in this cascade reaction, affording C2/C3-branched indolyl glycosides with high regio-/stereoselectivity. The utility of this protocol was also demonstrated by a large-scale reaction and diversified synthetic transformations of the desired products.
Topics & Concepts
StereoselectivityChemistryGlycosylationCombinatorial chemistryGlycosideReaction conditionsStereochemistryOrganic chemistryCatalysisBiochemistryCarbohydrate Chemistry and SynthesisSynthesis of Indole DerivativesSynthesis and Catalytic Reactions