Redox-mediated reactions of vinylferrocene: toward redox auxiliaries

Chemical redox reactions have been exploited to transformunreactive vinylferrocene into a powerful dienophile for the Diels–Alder reaction and reactive substrate for thiol addition reactionsupon conversion to its ferrocenium state. We have further investigatedthe ability of these reactions to facilitate redox-auxiliary-likereactivity by further hydrogenolyisis of the Diels–Alder adduct tothe corresponding cyclopentane derivative.