The michael reaction of silyl enol ethers with .ALPHA.,.BETA.-unsaturated ketones and acetals in the presence of titanium tetraalkoxide and titanium tetrachloride.
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概要
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Silyl enol ethers react with α,β-unsaturated ketones and esters in the presence of TiCl<SUB>4</SUB> or in the coexistence of TiCl<SUB>4</SUB> and Ti(O<I><SUP>i</SUP></I>-Pr)<SUB>4</SUB> to give 1,5-dicarbonyl compounds in good yields. The reactions of acetals derived from α,β-unsaturated ketones with silyl enol ethers in the coexistence of TiCl<SUB>4</SUB> and Ti(O<I><SUP>i</SUP></I>-Pr)<SUB>4</SUB>, followed by successive addition of 1,2-ethanedithiol, give the Michael products, δ-keto ethylene thioacetal, in good yields. The reaction of silyl enol ethers with acetals derived from α,β-unsaturated aldehydes also gives the Michael products when Ti(OCEt<SUB>3</SUB>)<SUB>4</SUB> is employed instead of Ti(O<I><SUP>i</SUP></I>-Pr)<SUB>4</SUB> in the above experiment and is successfully applied to the simple synthesis of dihydro rose oxide.
- 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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Soai Kenso
Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo
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Narasaka Koichi
Department Of Applied Chemistry Faculty Of Engineering Kyushu Institute Of Technology
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Aikawa Yukiko
Department of Chemistry, Faculty of Science, The University of Tokyo
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Narasaka Koichi
Department of Chemistry, Faculty of Science, The University of Tokyo
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