Ring opening of oxiranes by trimethylsilyl trifluoromethanesulfonate.
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概要
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Trimethylsilyl trifluoromethanesulfonate promotes ring opening reactions of oxirane derivatives. The reaction course is highly affected by the structures and substitution pattern of the substrates. Tetra-, tri-, and 2,2-disubstituted oxiranes and simple cycloalkene oxides are converted to the corresponding allylic alcohol trimethylsilyl ethers. The overall transformation is interpreted in terms of trans addition of the silyl trifluoromethanesulfonate to the oxirane ring followed by base-promoted anti elimination of a trifluoromethanesulfonic acid element. 2,3-Dialkyl- or monoalkyloxiranes isomerize to the corresponding ketones and aldehydes, respectively. (<I>Z</I>)-Cyclooctene oxide undergoes the transannular reaction to give <I>endo</I>-<I>cis</I>-2-trimethylsiloxybicyclo[3.3.0]octane. The reaction of 6-methyl-5-hepten-2-one oxide produces 2,2,6-trimethyl-3-trimethylsiloxy-3,4-dihydro-2<I>H</I>-pyran. 1,2-Methyl migration takes place in the reaction of (<I>E</I>)-3α-<I>t</I>-butyldimethylsiloxy-5α-pregnene 17α,20-oxide to afford 3α-<I>t</I>-butyldimethylsiloxy-17β-methyl-17α-[1-(trimethylsiloxy)ethyl]-18-nor-5α-androst-13(14)-ene. α-Pinene oxide gives <I>trans</I>-carveol trimethylsilyl ether.
- 公益社団法人 日本化学会の論文
著者
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Suzuki Masaaki
Department Of Atherosclerosis Metabolism And Clinical Nutrition National Cardiovascular Center
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Noyori Ryoji
Department Of Chemistry And Molecular Chirality Research Unit Nagoya University
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Murata Sizuaki
Department of Chemistry, Nagoya University
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