Ferrier-type alkynylation reaction mediated by indium

Org Lett. 2007 Aug 30;9(18):3679-82. doi: 10.1021/ol701480x. Epub 2007 Aug 2.

Abstract

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