title: HF-Induced Intramolecular C-Arylation and C-Alkylation/Fluorination of 2-Aminoglycopyranoses.
abstract: Internal C-aryl and C-alkyl glycosides derived from 2-aminoglycopyranoses have been synthesized, exploiting a HF-mediated stereoselective intramolecular glycosylation. These conditions are compatible with acetate protecting groups and allow introduction of aromatics with various electronic distributions at the anomeric position. This strategy also provides straightforward entry to original fluorinated sugar-azacycle hybrids via a tandem internal C-glycosylation/fluorination reaction starting from 2-N-allyl/propargyl glycopyranoses. All cyclizations proceed in a 1,2-cis stereocontrolled manner.
authors.affiliation: IC2MP, UMR-CNRS 7285, Equipe Synthèse organique, Bât. B28, 4 rue Michel Brunet, TSA 51106, Poitiers 86073 Cedex 9, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Probst
authors.affiliation: IC2MP, UMR-CNRS 7285, Equipe Synthèse organique, Bât. B28, 4 rue Michel Brunet, TSA 51106, Poitiers 86073 Cedex 9, France.
authors.forename: Amélie
authors.initials: A
authors.lastname: Martin
authors.affiliation: IC2MP, UMR-CNRS 7285, Equipe Synthèse organique, Bât. B28, 4 rue Michel Brunet, TSA 51106, Poitiers 86073 Cedex 9, France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Désiré
authors.affiliation: IC2MP, UMR-CNRS 7285, Equipe Synthèse organique, Bât. B28, 4 rue Michel Brunet, TSA 51106, Poitiers 86073 Cedex 9, France.
authors.forename: Agnès
authors.initials: A
authors.lastname: Mingot
authors.affiliation: Institut Lavoisier de Versailles, UMR CNRS 8180, 45 avenue des Etats-Unis, Versailles78035 Cedex, France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Marrot
authors.affiliation: IC2MP, UMR-CNRS 7285, Equipe Synthèse organique, Bât. B28, 4 rue Michel Brunet, TSA 51106, Poitiers 86073 Cedex 9, France.
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
authors.affiliation: IC2MP, UMR-CNRS 7285, Equipe Synthèse organique, Bât. B28, 4 rue Michel Brunet, TSA 51106, Poitiers 86073 Cedex 9, France.
authors.forename: Sébastien
authors.identifier: 0000-0002-6246-5829
authors.initials: S
authors.lastname: Thibaudeau