Boron-Promoted Umpolung Reaction of Sulfonyl Chlorides for the Stereospecific Synthesis of Thioglycosides via Reductive Deoxygenation Coupling Reactions
Siyu Li, Yujuan Wang, Lei Zhong, Siyu Wang, Zhengli Liu, Yuanwei Dai, Yun He, Feng Zhang
Abstract
glycoside counterparts and thus are of great therapeutic potential. Herein we disclose an efficient method for the stereospecific synthesis of 1-thioglycosides via a boron-promoted reductive deoxygenation coupling reaction from readily accessible sulfonyl chlorides and glycosyl bromides. Our protocol features mild conditions and excellent functional group tolerance and stereoselectivity. The translational potential of this metal-free approach is demonstrated by the late-stage glycodiversification of natural products and drug molecules.
Topics & Concepts
ChemistryUmpolungDeoxygenationGlycosylSulfonylStereoselectivityCoupling reactionCombinatorial chemistryStereospecificityFunctional groupOrganic chemistryCatalysisNucleophileAlkylPolymerCarbohydrate Chemistry and SynthesisSulfur-Based Synthesis TechniquesChemical Synthesis and Reactions