Synthesis of 1-hydrocarbon substituted cyclopropyl silyl ketones |
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Authors: | Mitsunori Honda Sho Sasaki Tsuyoshi Nishimoto Hiromoto Koshiro Ko-Ki Kunimoto Masahito Segi |
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Affiliation: | Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa 920-1192, Japan |
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Abstract: | The synthesis of cyclopropyl silyl ketones possessing a hydrocarbon group at 1-position of three-membered ring was investigated. The reaction of sulfoxonium ylide with α,β-unsaturated acylsilanes derived from α,β-unsaturated aldehydes did not afford the desired acylsilane derivatives. Instead, the corresponding silyl enol ethers were yielded exclusively. On the other hand, the Corey-Chaykovsky cyclopropanation of α-substituted α,β-unsaturated aldehydes proceeded well to give 1-substituted cyclopropyl aldehydes. The silyl substitution of formyl proton in the obtained aldehydes via umpolung of carbonyl group afforded the target acylsilanes. |
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Keywords: | Cyclopropyl silyl ketone α,β-Unsaturated aldehyde Sulfoxonium ylide Cyclopropanation Umpolung |
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