An efficient synthesis of cyclopropyl silyl ketones |
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Authors: | Mitsunori Honda Kenta NakaeToshiaki Nishizawa Mitsuhiro SudaKo-Ki Kunimoto Masahito Segi |
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Affiliation: | 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: | The reaction of silylcyclopropyl bromides with dichloromethyl methyl ether in the presence of n-butyllithium is investigated. Under basic reaction conditions, the corresponding cyclopropylidene derivatives are exclusively obtained. The resulting cyclopropylidene compounds are subjected to protonolysis or trapping with electrophiles in a one-pot to give the cyclopropyl silyl ketone derivatives in good yields. Acidic treatment of derived cyclopropyl silyl ketone allows isomerization to give the thermodynamically favorable trans form exclusively. |
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