DOI: 10.1021/acs.orglett.6c04358 ISSN: 1523-7060
Stereoselective Palladium-Catalyzed C(sp3)-H Arylation of Furanose Carboxamides
Linlin Li, Mayssa Zayene, Franck Le Bideau, Pascal Retailleau, Vincent Gandon, Angélique Ferry, Samir MessaoudiAbstract
We report the first stereoselective palladium-catalyzed C(sp3)–H arylation of furanose carboxamides at the C3 position, achieving 2,3-cis selectivity without prefunctionalization. Optimized conditions provide diverse arylated furanosides in yields up to 61%, and we established efficient protocols for removing the directing group and deprotecting benzyl groups. DFT calculations rationalize the stereochemical outcome, and this method enables access to suzetrigine analogs, expanding the synthetic toolkit for carbohydrate-based drug discovery.