期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 69, 期 24, 页码 8537-8540出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo0485536
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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.
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