Nature Communications (Nov 2018)

Differentiation between enamines and tautomerizable imines in the oxidation reaction with TEMPO

  • Xiaoming Jie,
  • Yaping Shang,
  • Zhe-Ning Chen,
  • Xiaofeng Zhang,
  • Wei Zhuang,
  • Weiping Su

DOI
https://doi.org/10.1038/s41467-018-07534-x
Journal volume & issue
Vol. 9, no. 1
pp. 1 – 10

Abstract

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Tautomerization of imines into enamines is the basis of their similar reactivity; however, minor structural changes may lead to different outcomes. Here, the authors show that the reaction of cyclohexanone and amines in presence of TEMPO affords either α-amino-enones or arylamines depending on the intermediate imine structure.