Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes

Akira Yoshimura, Khiem C. Nguyen, Gregory T. Rohde, Pavel S. Postnikov, Mekhman S. Yusubov, Viktor V. Zhdankin

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10 Scopus citations

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 (US)
Pages (from-to)11742-11751
Number of pages10
JournalJournal of Organic Chemistry
Volume82
Issue number22
DOIs
StatePublished - Nov 17 2017

Bibliographical note

Funding Information:
This work was supported by research grants from the National Science Foundation (CHE-1262479) and the Russian Science Foundation (RSF-16-13-10081).

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