Synthesis of hexahydrocyclopenta[c]furans by an intramolecular iron-catalyzed ring expansion reaction

Article abstract of DOI:10.1002/adsc.200700035

The intramolecular iron-catalyzed ring expansion reaction of epoxyalkenes was investigated with a preformed iron(salen) [Fe(Salen)] complex. The formal insertion of the alkene into the epoxide generated hexahydrocyclopenta[c]furan derivatives in moderate to good yields and diastereoselectivities depending on other functional groups present in the starting materials. In addition, oxygen-tethered epoxyalkenes were used for the synthesis of lignan isomers. The scope and limitations of the Fe (Salen)-catalyzed process of the reaction are discussed.