Remarkable Enhancement of Nucleophilicity of Tin Enolates toward Nitro- or Cyanoalkenes by Tetrabutylammonium Halides

The reaction of tin enolates with nitroalkenes was effectively catalyzed by tetrabutylammonium bromide (Bu4NBr) to give γ-nitroketones. When the substituted tin enolates at the β-carbon in the olefinic moiety were used, the diastereoselective addition proceeded through the acyclic transition state....

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Published in:Chemistry letters 2000-11, Vol.29 (11), p.1266-1267
Main Authors: Yasuda, Makoto, Ohigashi, Noriyuki, Baba, Akio
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Language:English
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creator Yasuda, Makoto
Ohigashi, Noriyuki
Baba, Akio
description The reaction of tin enolates with nitroalkenes was effectively catalyzed by tetrabutylammonium bromide (Bu4NBr) to give γ-nitroketones. When the substituted tin enolates at the β-carbon in the olefinic moiety were used, the diastereoselective addition proceeded through the acyclic transition state. Tetrabutylammonium chloride (Bu4NCl) strongly accelerated the reaction with the cyanoalkene to give the γ-cyanoketone.
doi_str_mv 10.1246/cl.2000.1266
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title Remarkable Enhancement of Nucleophilicity of Tin Enolates toward Nitro- or Cyanoalkenes by Tetrabutylammonium Halides
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