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HF-Induced Intramolecular C-Arylation and C-Alkylation/Fluorination of 2-Aminoglycopyranoses
Nicolas Probst1, Amélie Martin1, Jérôme Désiré1
1IC2MP, UMR-CNRS 7285, Equipe Synthèse organique, Bât. B28, 4 rue Michel Brunet, TSA 51106, Poitiers 86073 Cedex 9, France.
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.
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