Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis

Saki Uraoka, Ikumi Shinohara, Hisato Shimizu, Keiichi Noguchi, Akira Yoshimura, Viktor V. Zhdankin, Akio Saito

Research output: Contribution to journalArticle


As a first non-metal-catalyzed oxidation for the in situ generation of acylnitroso species, we describe the hypoiodite catalysis using tetra-n-butylammonium iodide as precatalyst with tert-butyl hydroperoxide or hydrogen peroxide as a terminal oxidant. This method can be applied to hetero Diels–Alder (HDA) reactions with dienes and ene reactions with alkenes. Furthermore, the conversions of the representative HDA adduct to nitrone and 2-amino alcohols were demonstrated. Compared with previous metal-catalyzed oxidation methods, this work provides a more efficient and environmentally friendly procedure.

Original languageEnglish
Pages (from-to)6199-6203
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number45
Publication statusPublished - 6 Dec 2018



  • Acylnitroso
  • Catalysis
  • Cycloaddition
  • Ene reaction
  • Iodine

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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