Diversity-Oriented Synthesis of 2,5-Disubstituted Tetrahydrofurans Based on a “Cyclization-Hydrogenation-Substitution” Strategy

A variety of (tetrahydrofuran-2-yl)acetates have been prepared based on hydrogenation and subsequent nucleophilic substitutions of 2-alkylidene-5-(hydroxymethyl)tetrahydrofurans. The latter are readily available by cyclization of 1,3-dicarbonyl dianions (“free dianions”) with epibromohydrin. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)