Synthesis and Use of Achiral Oxazolidine-2-thiones in Selective Preparation oftrans2,5-Disubstituted Tetrahydrofurans

The use of achiral N-acetyloxazolidine-2-thiones in the C-glycosylation of lactol acetates has allowed us to prepare with high diastereoselectivity the expected trans 2,5-disubstituted tetrahydrofurans. A study based on the role of the steric hindrance of the N-acetyloxazohdine-2-thiones is reported. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)