Acid-catalyzed reaction behavior of 1-silylcyclopropylmethanols |
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| Authors: | Mitsunori Honda Takahito Mita Toshiaki Nishizawa Toru Sano Masahito Segi Tadashi Nakajima |
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| Institution: | Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa 920-1192, Japan |
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| Abstract: | Treatment of 1-silylcyclopropylmethanols with TsOH in methanol gives different homoallyl ethers depending upon the configuration of substituents on cyclopropane ring and the kinds of substituents on carbinyl carbon. Especially, the reaction of cyclopropylmethanols having no substituents on the same side with silyl group on cyclopropane ring proceeds to give the corresponding E-homoallyl ethers with high stereoselectivity. The following protiodesilylation of resulting homoallyl ethers proceeds with retention of configuration. |
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| Keywords: | Cyclopropylmethanol Homoallylic rearrangement Trimethylsilyl group Protiodesilylation |
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