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Ring-Opening Cycloaddition of Aziridines to Ketenimines
Heiko Maas1, Corinne Bensimon, Howard Alper
1Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
The Journal of Organic Chemistry
|October 25, 2001
Abstract:
The Lewis acid-catalyzed addition of aziridines to ketenimines gave substituted pyrrolidonimines in 47-87% yields. The hard Lewis acid LiClO(4) proved to be superior to the soft [(PhCN)(2)PdCl(2)], affording higher yields under milder conditions. The reaction is regioselective and occurs with complete stereoselectivity using [(PhCN)(2)PdCl(2)] and with a small amount of racemization in the case of LiClO(4).