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

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

Keywords

Acylnitroso
Catalysis
Cycloaddition
Ene reaction
Iodine

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201801340

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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 › peer-review

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AU - Uraoka, Saki

AU - Shinohara, Ikumi

AU - Shimizu, Hisato

AU - Noguchi, Keiichi

AU - Yoshimura, Akira

AU - Zhdankin, Viktor V.

AU - Saito, Akio

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KW - Catalysis

KW - Cycloaddition

KW - Ene reaction

KW - Iodine

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