Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl β- C -Glycosides

Nicolas Guisot (1) , Idriss Ella Obame (1) , Prathap Ireddy (1) , Arnaud Nourry (1) , Christine Saluzzo (1) , Gilles Dujardin (1) , Didier Dubreuil (2) , Muriel Pipelier (2) , Stéphane Guillarme (1)

1 IMMM - Institut des Molécules et Matériaux du Mans
2 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

A new strategy for the synthesis of acyl β-C-glycosides is described. The reactivity of glyconitriles toward organometallic reagents such as organomagnesium or organolithium derivatives was studied, affording acyl β-C-glycosides in moderate to good yields. In this study, glycal formation was efficiently prevented by deprotonating the hydroxyl group in position 2 of the glyconitriles during the process.

Mots clés: Acyls; Carbon; Inorganic carbon compounds; Ketones; Reagents

Domaines: Chimie organique

Nicolas Guisot, Idriss Ella Obame, Prathap Ireddy, Arnaud Nourry, Christine Saluzzo, et al.. Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl β- C -Glycosides. Journal of Organic Chemistry, 2016, 81 (6), pp.2364-2371. ⟨10.1021/acs.joc.5b02853⟩. ⟨hal-02117201⟩