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 | |
| 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
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
}
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
VL - 2018
SP - 6199
EP - 6203
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 45
ER -