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- Title
Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis.
- Authors
Uraoka, Saki; Shinohara, Ikumi; Shimizu, Hisato; Noguchi, Keiichi; Yoshimura, Akira; Zhdankin, Viktor V.; Saito, Akio
- 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. First example of hypoiodite‐catalyzed oxidation for the in situ generation of acylnitroso species, which can be used in hetero Diels–Alder reactions with dienes and in ene reactions with alkenes.
- Subjects
DIELS-Alder reaction; HYPOIODITES; CATALYSIS; ENE reactions; OXIDATION; HYDROGEN peroxide; DIOLEFINS; ALKENES
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 45, p6199
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201801340