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Synthesis of α-Substituted Allylic Amines via a Modified Bruylants Reaction

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journal contribution
posted on 17.06.2000, 00:00 by Claude Agami, François Couty, Gwilherm Evano
Silver tetrafluoroborate, used as an iminium ion promoter from α-amino nitriles, is an efficient additive in the Bruylants reaction involving vinylic Grignards. Improved yields of allylic amines were obtained when the starting α-amino nitrile was treated with this silver salt prior to its reaction with the vinylic Grignard. This improvement was not observed in the case of acetylenic Grignards. The reactivity of other vinyl organometallics (M = Zn, Li, Al, Cu, Si) was briefly examined.