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 output: Contribution to journalArticle

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

Fingerprint

Catalysis
catalysis
Amino Alcohols
tert-Butylhydroperoxide
Oxidation
oxidation
Alkenes
peroxides
Iodides
dienes
hydrogen peroxide
Oxidants
Hydrogen Peroxide
iodides
adducts
alkenes
alcohols
Metals
metals
hypoiodous acid

Keywords

  • Acylnitroso
  • Catalysis
  • Cycloaddition
  • Ene reaction
  • Iodine

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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 journalArticle

Uraoka, Saki ; Shinohara, Ikumi ; Shimizu, Hisato ; Noguchi, Keiichi ; Yoshimura, Akira ; Zhdankin, Viktor V. ; Saito, Akio. / Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis. In: European Journal of Organic Chemistry. 2018 ; Vol. 2018, No. 45. pp. 6199-6203.
@article{2f3585ad7cb94083872713acebe5c71d,
title = "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.",
keywords = "Acylnitroso, Catalysis, Cycloaddition, Ene reaction, Iodine",
author = "Saki Uraoka and Ikumi Shinohara and Hisato Shimizu and Keiichi Noguchi and Akira Yoshimura and Zhdankin, {Viktor V.} and Akio Saito",
year = "2018",
month = "12",
day = "6",
doi = "10.1002/ejoc.201801340",
language = "English",
volume = "2018",
pages = "6199--6203",
journal = "Annalen der Pharmacie",
issn = "0075-4617",
publisher = "Wiley-VCH Verlag",
number = "45",

}

TY - JOUR

T1 - Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis

AU - Uraoka, Saki

AU - Shinohara, Ikumi

AU - Shimizu, Hisato

AU - Noguchi, Keiichi

AU - Yoshimura, Akira

AU - Zhdankin, Viktor V.

AU - Saito, Akio

PY - 2018/12/6

Y1 - 2018/12/6

N2 - 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.

AB - 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.

KW - Acylnitroso

KW - Catalysis

KW - Cycloaddition

KW - Ene reaction

KW - Iodine

UR - http://www.scopus.com/inward/record.url?scp=85055934877&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85055934877&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201801340

DO - 10.1002/ejoc.201801340

M3 - Article

AN - SCOPUS:85055934877

VL - 2018

SP - 6199

EP - 6203

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 45

ER -