Stereoselective C-Glycosylation Reactions with Arylzinc Reagents

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. Ste...

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Bibliographic Details
Published in:Organic letters 2012-03, Vol.14 (6), p.1480-1483
Main Authors: Lemaire, Sébastien, Houpis, Ioannis N, Xiao, Tingting, Li, Juanjuan, Digard, Eric, Gozlan, Charlotte, Liu, Renmao, Gavryushin, Andrey, Diène, Coura, Wang, Youchu, Farina, Vittorio, Knochel, Paul
Format: Article
Language:English
Subjects:
Benzhydryl Compounds
Glucosides - chemical synthesis
Glucosides - chemistry
Indicators and Reagents - chemistry
Molecular Structure
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300220p