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

doi:10.1002/ejoc.201901258

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

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

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 language	English (US)
Pages (from-to)	6682-6689
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	39
DOIs	https://doi.org/10.1002/ejoc.201901258
State	Published - Oct 24 2019

Bibliographical note

Funding Information:
This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081-P), the Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-69/2019) and National Science Foundation ((CHE-1759798). A. S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199).

Publisher Copyright:
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Aldoximes
Cycloaddition
Hypervalent iodine(III) reagents
Isoxazoles
Regioselectivity

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title = "Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones",

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.",

keywords = "Aldoximes, Cycloaddition, Hypervalent iodine(III) reagents, Isoxazoles, Regioselectivity",

author = "Akira Yoshimura and Jarvi, {Melissa E.} and Shea, {Michael T.} and Makitalo, {Cody L.} and Rohde, {Gregory T.} and Yusubov, {Mekhman S.} and Akio Saito and Zhdankin, {Viktor V.}",

note = "Funding Information: This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081-P), the Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-69/2019) and National Science Foundation ((CHE-1759798). A. S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199). Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/ejoc.201901258",

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T1 - Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

AU - Yoshimura, Akira

AU - Jarvi, Melissa E.

AU - Shea, Michael T.

AU - Makitalo, Cody L.

AU - Rohde, Gregory T.

AU - Yusubov, Mekhman S.

AU - Saito, Akio

AU - Zhdankin, Viktor V.

N1 - Funding Information: This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081-P), the Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-69/2019) and National Science Foundation ((CHE-1759798). A. S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199). Publisher Copyright: © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/10/24

Y1 - 2019/10/24

N2 - 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.

AB - 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.

KW - Aldoximes

KW - Cycloaddition

KW - Hypervalent iodine(III) reagents

KW - Isoxazoles

KW - Regioselectivity

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

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