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

Результат исследований: Материалы для журналаСтатья

Аннотация

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.

Язык оригиналаАнглийский
Страницы (с-по)6199-6203
Число страниц5
ЖурналEuropean Journal of Organic Chemistry
Том2018
Номер выпуска45
DOI
СостояниеОпубликовано - 6 дек 2018

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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