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)|
|Number of pages||10|
|Journal||Journal of Organic Chemistry|
|State||Published - Nov 17 2017|
Bibliographical noteFunding Information:
This work was supported by research grants from the National Science Foundation (CHE-1262479) and the Russian Science Foundation (RSF-16-13-10081).
© 2017 American Chemical Society.