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Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones
Author(s) -
Yoshimura Akira,
Jarvi Melissa E.,
Shea Michael T.,
Makitalo Cody L.,
Rohde Gregory T.,
Yusubov Mekhman S.,
Saito Akio,
Zhdankin Viktor V.
Publication year - 2019
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.201901258
Subject(s) - hypervalent molecule , chemistry , regioselectivity , cycloaddition , reagent , nitrile , isoxazole , iodine , organic chemistry , chemoselectivity , iodide , medicinal chemistry , combinatorial chemistry , catalysis
An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from respective aldoximes using hypervalent iodine reagents has been developed. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective cycloaddition reaction resulting in the formation of the 3,4‐disubstituted isoxazoles in moderate to good yields. Structures of several isoxazole products were confirmed by a single X‐ray crystallography.