Synthesis of axially chiral biaryl thioglycosides through thiosugar-directed Pd-catalyzed asymmetric C–H activation. Issue 80 (17th September 2021)

• Record Type: Journal Article
• Authors: Fatthalla, Maha; Grimblat, Nicolas; Brachet, Etienne; Alami, Mouad; Gandon, Vincent; Le Bideau, Franck; Messaoudi, Samir
• Is Part Of: Chemical communications. Volume 57:Issue 80(2021)
• Page Start: 10355
• Page End: 10358
• Publication Date: 2021-09-17
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc03971g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An atroposelective Fujiwara–Moritani reaction towards the synthesis of alkenylthioglycoside is reported. β-thioglucose moiety is used both as a directing group for the C–H bond activation and as a chiral source inducing axial chirality. Abstract : Herein we report for the first time that the thiosugar moiety can be used both as a directing group enabling the regioselective activation of a C–H bond of biaryl scaffolds and as a chiral source inducing axial chirality. Our approach enables the easy generation of complex thioglycoside atropoisomers, thus paving the way to new products of potential biological interest.