Ferrier-Type Alkynylation Reaction
Mediated by Indium

Lubin-Germain, Nadège; Hallonet, Agnès; Huguenot, Florent; Palmier, Sara; Uziel, Jacques; Augé, Jacques

doi:10.1021/ol701480x.s008

ol701480x_si_008.pdf (3.23 MB)

Ferrier-Type Alkynylation Reaction Mediated by Indium

journal contribution

posted on 2007-08-30, 00:00 authored by Nadège Lubin-Germain, Agnès Hallonet, Florent Huguenot, Sara Palmier, Jacques Uziel, Jacques Augé

An efficient Ferrier-type alkynylation reaction between glycals and iodoalkynes using Barbier conditions is described. These conditions require In⁰, In^I, or In^II and lead to α-2,3-unsaturated-C-glycosides with good stereoselectivity. When glycosyliodoalkynes are used, trehalose-derived compounds and α-(1→6)-C-disaccharides are obtained.