Ring-closing reaction of allenic/propargylic anions generated by base treatment of sulfonylallenes |
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Authors: | Kitagaki Shinji Teramoto Satoshi Mukai Chisato |
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Affiliation: | Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. |
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Abstract: | The intramolecular trapping of allenyl/propargyl anions generated by base treatment of sulfonylallenes was investigated. Treatment of 1-(omega-iodoalkyl)-1-(phenylsulfonyl)allenes with TBAF or NaH in DMF efficiently produced three- to seven-membered 1-ethynyl-1-(phenylsulfonyl) substituted carbocycles. The allenyl/propargyl anions could also be intramolecularly trapped using a terminal aldehyde or alpha,beta-unsaturated ester. The phenylsulfonyl group was found to be replaced by other electron-withdrawing functionalities like ketone and ester groups but not by an alkyl group for this novel ring-closing reaction. |
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