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Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis
Author(s) -
Uraoka Saki,
Shinohara Ikumi,
Shimizu Hisato,
Noguchi Keiichi,
Yoshimura Akira,
Zhdankin Viktor V.,
Saito Akio
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801340
Subject(s) - chemistry , catalysis , adduct , hydrogen peroxide , ene reaction , organic chemistry , diels–alder reaction , iodide , tetra , medicinal chemistry
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.