Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

Akira Yoshimura, Melissa E. Jarvi, Michael T. Shea, Cody L. Makitalo, Gregory T. Rohde, Mekhman S. Yusubov, Akio Saito, Viktor V. Zhdankin

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)6682-6689
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number39
DOIs
Publication statusPublished - 24 Oct 2019

Fingerprint

Isoxazoles
Oximes
Cycloaddition
cycloaddition
Iodine
iodine
reagents
Nitriles
X ray crystallography
nitriles
Oxides
crystallography
benzene
oxides
products
x rays
(hydroxy(tosyloxy)iodo)benzene

Keywords

  • Aldoximes
  • Cycloaddition
  • Hypervalent iodine(III) reagents
  • Isoxazoles
  • Regioselectivity

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones. / Yoshimura, Akira; Jarvi, Melissa E.; Shea, Michael T.; Makitalo, Cody L.; Rohde, Gregory T.; Yusubov, Mekhman S.; Saito, Akio; Zhdankin, Viktor V.

In: European Journal of Organic Chemistry, Vol. 2019, No. 39, 24.10.2019, p. 6682-6689.

Research output: Contribution to journalArticle

Yoshimura, Akira ; Jarvi, Melissa E. ; Shea, Michael T. ; Makitalo, Cody L. ; Rohde, Gregory T. ; Yusubov, Mekhman S. ; Saito, Akio ; Zhdankin, Viktor V. / Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 39. pp. 6682-6689.
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AU - Rohde, Gregory T.

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