Ring-Closing Reaction of Allenic/Propargylic Anions Generated by Base Treatment of Sulfonylallenes

Ring-Closing Reaction of Allenic/Propargylic Anions Generated by Base Treatment of Sulfonylallenes

The intramolecular trapping of allenyl/propargyl anions generated by base treatment of sulfonylallenes was investigated. Treatment of 1-(ω-iodoalkyl)-1-(phenylsulfonyl)allenes with TBAF or NaH in DMF efficiently produced three- to seven-membered 1-ethynyl-1-(phenylsulfonyl) substituted carbocycles....

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Veröffentlicht in:Organic letters 2007-06, Vol.9 (13), p.2549-2552
Hauptverfasser: Kitagaki, Shinji, Teramoto, Satoshi, Mukai, Chisato
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creator Kitagaki, Shinji
Teramoto, Satoshi
Mukai, Chisato
description The intramolecular trapping of allenyl/propargyl anions generated by base treatment of sulfonylallenes was investigated. Treatment of 1-(ω-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 α,β-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.
doi_str_mv 10.1021/ol0709329
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title Ring-Closing Reaction of Allenic/Propargylic Anions Generated by Base Treatment of Sulfonylallenes
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