Stereoselective syntheses of .ALPHA.-substituted cyclic ethers and syn-1,3-diols.
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概要
- 論文の詳細を見る
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-(<I>t</I>-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 (−)-<I>cis</I>-rose oxide and (<I>cis</I>-6-methyltetrahydro-2-pyranyl)acetic acid, a constitutent of civet. Furthermore, <I>syn</I>-1,3-diols are also stereoselectively prepared from lactone analogue, 6-<I>cis</I>-substituted 2-trichloromethyl-1,3-dioxan-4-ones, easily prepared from β-hydroxy carboxylic acids.
- 公益社団法人 日本化学会の論文
著者
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Mukaiyama Teruaki
Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo
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HOMMA KOICHI
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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Takenoshita Haruhiro
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo
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