Hypervalent Iodine Catalyzed Generation of Nitrile Oxides from Oximes and their Cycloaddition with Alkenes or Alkynes
Akira Yoshimura*, Kyle R. Middleton, Anthony D. Todora, Brent J. Kastern, Steven R. Koski, Andrey V. Maskaev and Viktor V. Zhdankin*
*Department of Chemistry and Biochemistry, University of Minnesota—Duluth, Duluth, Minnesota, 55812, United States, Email: ayoshimud.umn.edu, vzhdankid.umn.edu
A. Yoshimura, K. R. Middleton, A. D. Todora, B. J. Kastern, S. R. Koski, A. V. Maskaev, V. V. Zhdankin, Org. Lett., 2013, 15, 4010-4013.
DOI: 10.1021/ol401815n
see article for more reactions
Abstract
A hypervalent iodine species, which is formed in situ in the presence of oxone as terminal oxidant, catalyzes the oxidation of aldoximes to generate nitrile oxides. A subsequent reaction with alkenes gives the corresponding isoxazolines in good yields, whereas the reaction with alkynes gives the corresponding isoxazoles in moderate yields.
see article for more examples
Key Words
isoxazolines, oxone, hypervalent iodine compounds
ID: J54-Y2013