[R ₄N] [AOT]: A surfactant ionic liquid as a mild glycosylation promoter

[RN ₄][AOT] is a versatile surfactant ionic liquid that can be used in combination with N-Iodosuccinimide to promote the room temperature glycosylation of thiophenyl glycoside donors. The conditions are mild, with no requirement for molecular sieves, and are compatible with a wide range of donors and protecting groups. Under these conditions, a different range of disaccharides have been obtained in good to excellent yields and good stereoselectivities. Furthermore, the anomeric outcome of the glycosylation reaction using glycosyl donors with no participating group at C-2 could be tuned by switching the solvent from DCM to MeCN. © 2011 Copyright Taylor and Francis Group, LLC.