Abstract The assembly of (Z)-chloro-exo-methylenetetrahydrofurans by an original and connective anionic cascade sequence is reported. Base-catalysed condensation of β- hydroxyketones with 1, 1-dichloroethylene generates, in moderate to good yields, the corresponding (Z)-chloro-exo-methylenetetrahydrofurans. Acidic treatment of this motif leads to several unexpected dimers, possessing unique structural features.
