A formal [4 + 2] cyclization of easily available ketene dithioacetals with acyl chlorides has been developed. Mediated by lithium bis(trimethylsilyl)amide, a series of γ-pyrones were obtained with a broad substrate scope. This unprecedented formal [4 + 2] cyclization provides a novel mode for ketene dithioacetals as versatile synthons. The synthesized γ-pyrones could be successfully transformed to 2-aryl/amino γ-pyrones and 2,3-dihydroimidazo[1,2-a]pyridin-7(1H)-ones mainly via the cleavage of the C-S bond.