[Figure not available: see fulltext.] Addition of primary amines to 1-phenyl-5-trimethylsilylpenta-1,4-diyn-3-one with subsequent cyclization affords 5-phenyl-2-(trimethylsilylmethylidene)-1,2-dihydro-3H-pyrrol-3-ones. Both electron-rich and electron-deficient anilines and alkyl amines provide regio- and stereoselective formation of single product in high yields. The two-step transformation benefits from full atom economy, operational simplicity, and no need for additives and catalysts.