Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes
- 31 July 2017
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 82 (22), 11742-11751
- https://doi.org/10.1021/acs.joc.7b01462
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.Keywords
Funding Information
- NSF (CHE-1262479)
- Russian Science Foundation (RSF-16-13-10081)
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