Iron-mediated intramolecular metalative cyclization of alpha,beta-unsaturated esters and amides. Versatile one-pot preparation of bicyclic ketoesters

2-Nonen-7-ynedioic or 2-decen-8-ynedioic acid derivatives were treated with an iron reagent generated from FeCl2 and t-BuMgCl in a ratio of 1:4 to give cyclized products after hydrolysis, deuteriolysis, or the addition of carbonyl compounds. Upon reaction with the same iron reagent, 2,7-nonadienedioates afforded bicyclic ketoesters (and their enol forms) after the addition of s-BuOH or carbonyl compounds.