Iodine (III)-Mediated Intramolecular Cyclization of Hydroxy Allylsilanes : Synthesis of 5- or 6-Membered β-Methylene Cyclic Ethers

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Oxidative cyclization of hydroxy allylsilanes utilizing the combination of a hypervalent organoiodine compound and a Lewis acid was studied. The allylsilanes 4,prepared from the γ-lactones 1 via conversion to the bis (trimethylsilylmethyl) carbinols 3,on treatment with iodosyl-benzene in the presence of boron trifluoride-etherate in an ethereal solution, afforded the 6-membered β-methylene cyclic ethers 13a and 13b in good yields. Similar treatment of the allylsilanes 8a and 8b gave the 5-membered cyclic ethers 13a and 13b. On the other hand, oxidative cyclization of the carboxylic acid 12 gave a poor yield of the lactone 21 and the major product was found to be the rearranged γ-keto acid 22. Regioselectivity in the iodine (III)-mediated cyclization of 8a is discussed.

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