Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

An efficient cycloaddition of heterocyclic alkenes with nitrile oxides generated in situ from the corresponding aldoximes using organohypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (Koser's reagent), has been developed. The oxidative cyclization of various aldoximes with 1-propene-1,3-sultone affords the respective isoxazoline-ring-fused heterobicyclic products in moderate to good yields. Furthermore, the reaction of aldoxime with a cyclic phospholene-oxide under similar conditions produces the corresponding heterobicyclic phospholene oxides in moderate yields. The structures of bicyclic phospholene oxide and two sultones were established by single-crystal X-ray crystallography.

Original languageEnglish
Pages (from-to)11742-11751
Number of pages10
JournalJournal of Organic Chemistry
Volume82
Issue number22
DOIs
Publication statusPublished - 17 Nov 2017

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Oximes
Alkenes
Iodine
Oxides
Nitriles
Cycloaddition
X ray crystallography
Cyclization
Single crystals
naphthosultone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes. / Yoshimura, Akira; Nguyen, Khiem C.; Rohde, Gregory T.; Postnikov, Pavel S.; Yusubov, Mekhman S.; Zhdankin, Viktor V.

In: Journal of Organic Chemistry, Vol. 82, No. 22, 17.11.2017, p. 11742-11751.

Research output: Contribution to journalArticle

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AU - Nguyen, Khiem C.

AU - Rohde, Gregory T.

AU - Postnikov, Pavel S.

AU - Yusubov, Mekhman S.

AU - Zhdankin, Viktor V.

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AB - An efficient cycloaddition of heterocyclic alkenes with nitrile oxides generated in situ from the corresponding aldoximes using organohypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (Koser's reagent), has been developed. The oxidative cyclization of various aldoximes with 1-propene-1,3-sultone affords the respective isoxazoline-ring-fused heterobicyclic products in moderate to good yields. Furthermore, the reaction of aldoxime with a cyclic phospholene-oxide under similar conditions produces the corresponding heterobicyclic phospholene oxides in moderate yields. The structures of bicyclic phospholene oxide and two sultones were established by single-crystal X-ray crystallography.

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