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 School of Chemistry & Applied Biomedical Sciences

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	6199-6203
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	45
DOIs	https://doi.org/10.1002/ejoc.201801340
Publication status	Published - 6 Dec 2018

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Keywords

Acylnitroso
Catalysis
Cycloaddition
Ene reaction
Iodine

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Uraoka, S., Shinohara, I., Shimizu, H., Noguchi, K., Yoshimura, A., Zhdankin, V. V., & Saito, A. (2018). Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis. European Journal of Organic Chemistry, 2018(45), 6199-6203. https://doi.org/10.1002/ejoc.201801340

Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis. / Uraoka, Saki; Shinohara, Ikumi; Shimizu, Hisato; Noguchi, Keiichi; Yoshimura, Akira ; Zhdankin, Viktor V.; Saito, Akio.

In: European Journal of Organic Chemistry, Vol. 2018, No. 45, 06.12.2018, p. 6199-6203.

Research output: Contribution to journal › Article

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10.1002/ejoc.201801340