4.7 Article

Iron-Catalyzed Ring-Opening/Allylation of Cyclobutanone Oxime Esters with Allylic Sulfones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 9, Pages 1775-1779

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701630

Keywords

Allylation; cyclobutanone oxime esters; iron-catalyzed; radical; ring-opening reaction

Funding

  1. Natural Science Basic Research Plan in Shaanxi Province of China [2016JZ002]
  2. Fundamental Research Funds of the Central Universities [1191329724, xjj2016056, zrzd2017001]
  3. National Natural Science Foundation of China [21602168]

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An iron-catalyzed radical allylation of cyclobutanone oxime esters with allylic sulfones via C-C bond cleavage is reported. This protocol provides a straight-forward approach to cyanoalkylated alkenes with good functional group tolerance and high regioselectivity. Furthermore, this reaction can be further expanded to ring-opening of less-strained cyclopentanone oxime esters, leading to desired cyanoalkylated alkenes in good yields.

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