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An organocatalytic [4 + 2] cascade annulation of salicylaldehydes and 1,3-bisarylsulfonylpropenes has been developed. This protocol enables the efficient and straightforward synthesis of a new series of 3-sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes that are useful for exploring pharmacologically valued compounds. Further reductive modifications result in 3-desulfonylated chromene or chromane derivatives. This protocol can be expanded to the synthesis of 3-sulfonyl-2-sulfonylmethyl 1,2-dihydroquinoline.