Abstract Double nucleophilic addition reactions of dialkoxy ketenesilyl acetals proceeded with α, β-unsaturated imines to give 1, 4-and 1, 2-double addition products, and their subsequent transformations afforded multisubstituted pyrroles in good yields. Application of this procedure to the synthesis of an imidazole glycerol phosphate dehydratase inhibitor (IGPDI), a physiologically active 2, 3, 5-trisubstituted pyrrole, is also described.