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 (US) |
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Pages (from-to) | 11742-11751 |
Number of pages | 10 |
Journal | Journal of Organic Chemistry |
Volume | 82 |
Issue number | 22 |
DOIs | |
State | Published - 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).
Publisher Copyright:
© 2017 American Chemical Society.