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Regioselective cyclization reactions of 1,3-bis(silyloxy)-1,3-butadienes provide an elegant approach for the synthesis of various complex carba- and heterocycles. Thus, various bridged and non-bridged N-heterocycles, functionalized salicylates and pyran-4-ones are prepared based on cyclization reactions of 1,3-bis(silylenol ethers). Isochromanes and chromanes are prepared based on chelation-controlled cyclization of 1,3-bis(silylenol ethers) with 1,1-diacylcyclopropanes. In addition, 6-halomethyl-5,6-dihydro-4H-1,2-oxazines are synthesized by regioselective cyclization of arylalkenyl-oximes.