title: Stereoselective C-glycosylation reactions with arylzinc reagents.
abstract: 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.
authors.affiliation: Pharmaceutical Development and Manufacturing Sciences, Janssen Pharmaceutica, Turnhoutseweg 30, B-2340 Beerse, Belgium. slemaire@its.jnj.com
authors.forename: Sébastien
authors.initials: S
authors.lastname: Lemaire
authors.forename: Ioannis N
authors.initials: IN
authors.lastname: Houpis
authors.forename: Tingting
authors.initials: T
authors.lastname: Xiao
authors.forename: Juanjuan
authors.initials: J
authors.lastname: Li
authors.forename: Eric
authors.initials: E
authors.lastname: Digard
authors.forename: Charlotte
authors.initials: C
authors.lastname: Gozlan
authors.forename: Renmao
authors.initials: R
authors.lastname: Liu
authors.forename: Andrey
authors.initials: A
authors.lastname: Gavryushin
authors.forename: Coura
authors.initials: C
authors.lastname: Diène
authors.forename: Youchu
authors.initials: Y
authors.lastname: Wang
authors.forename: Vittorio
authors.initials: V
authors.lastname: Farina
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel
mesh_terms: D001559:Benzhydryl Compounds; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001559:Benzhydryl Compounds; D005960:Glucosides; D007202:Indicators and Reagents; C529054:dapagliflozin