The utilization of in situ generated zirconocene-benzyne complexes as a means to effect cis carbofunctionalizations of cyclic olefins in a one-pot procedure is described. The stereospecific insertion of cyclic olefins provides the cis-zirconaindane metallacycles exclusively. The intermediate metallacycles were treated with a variety of electrophiles to provide diasteroeselective syntheses of arylcyanoalkanes, tricyclic ketones, and 2,3-dihydrobenzo[b]thiophenes in moderate overall yields.