815575-41-8Relevant articles and documents
Lewis acid catalyzed dipolar cycloadditions of an activated imidate
Bowman, Roy K.,Johnson, Jeffrey S.
, p. 8537 - 8540 (2004)
An evaluation of simple Lewis acids revealed that N-malonylimidates undergo catalyzed [3+2] cycloaddition reactions with aldehydes, imines, and activated olefins to form oxazolines, imidazolines, and pyrrolines, respectively. Reactions proceed optimally at ambient temperature with the addition of 5 mol % of MgCl2 in CH3CN. Experiments aimed at elucidation of the reactive intermediate undergoing cycloaddition suggest that the Lewis acid promotes a 1,2-prototropic shift to give a metal-coordinated azomethine ylide, rather than ionization and proton transfer to give a nitrile ylide.