Stereoselective Syntheses of α-Substituted Cyclic Ethers and syn-1,3-Diols

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Abstract
In the presence of a catalytic amount of triphenylmethylium hexachloroantimonate or a catalyst system of antimony pentachloride, chlorotrimethylsilane and tin(II) iodide, α-substituted cyclic ethers are stereoselectively prepared from lactones by successive treatment with 1-(t-butyldimethylsiloxy)-1-ethoxyethene and silyl nucleophiles such as triethylsilane, allyltrimethylsilane and trimethylsilyl cyanide. These catalysts also promote the reaction of γ-, δ-, and ε-trimethylsiloxy carbonyl compounds with silyl nucleophiles resulting in the formation of α-substituted cyclic ethers. The former procedure is effectively applied to short syntheses of (−)-cis-rose oxide and (cis-6-methyltetrahydro-2-pyranyl)acetic acid, a constitutent of civet. Furthermore, syn-1,3-diols are also stereoselectively prepared from lactone analogue, 6-cis-substituted 2-trichloromethyl-1,3-dioxan-4-ones, easily prepared from β-hydroxy carboxylic acids.

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