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Stereoselective C-Glycosylation Reactions with Arylzinc Reagents

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journal contribution
posted on 16.03.2012, 00:00 by Sébastien Lemaire, Ioannis N. Houpis, Tingting Xiao, Juanjuan Li, Eric Digard, Charlotte Gozlan, Renmao Liu, Andrey Gavryushin, Coura Diène, Youchu Wang, Vittorio Farina, Paul Knochel
A general, transition-metal-free, highly stereoselective cross-coupling reaction between glycosyl bromides and various arylzinc reagents leading to β-arylated glycosides is reported. The stereoselectivity of the reaction is explained by invoking anchimeric assistance via a bicyclic intermediate. Stereochemical probes confirm the participation of the 2-pivaloyloxy group. Finally, this new method was applied to a short and efficient stereoselective synthesis of Dapagliflozin and Canagliflozin.