Highly diastereoselective radical addition–cyclization strategy: facile synthesis of substituted furans

Abstract

A novel strategy is described in which an intermolecular carbon-centered radical addition to a β-oxygenated acceptor followed by intramolecular cyclization leads to the formation of 2,3,4- and 2,3,4,5-substituted furan rings. Excellent levels of 2,4-trans selectivity are observed in accordance with the Beckwith–Houk model for selectivity in 5-exo radical cyclizations.