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 Zhdankin, Akio Saito

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

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 (US)
Pages (from-to)6199-6203
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number45
DOIs
StatePublished - Dec 6 2018

Bibliographical note

Funding Information:
This work was partially supported by JSPS Grants-in-Aid for Scientific Research (C) (Grant No 15K07852) and by JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199). A. Y. and V. V. Z. are thankful to Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-195/ 2018) and to Russian Science Foundation (RSF-16-13-10081).

Keywords

  • Acylnitroso
  • Catalysis
  • Cycloaddition
  • Ene reaction
  • Iodine

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