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 language | English |
|---|---|
| Pages (from-to) | 11742-11751 |
| Number of pages | 10 |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Issue number | 22 |
| DOIs | |
| Publication status | Published - 17 Nov 2017 |
ASJC Scopus subject areas
- Organic Chemistry
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Yoshimura, A., Nguyen, K. C., Rohde, G. T., Postnikov, P. S., Yusubov, M. S., & Zhdankin, V. V. (2017). Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes. Journal of Organic Chemistry, 82(22), 11742-11751. https://doi.org/10.1021/acs.joc.7b01462